Win A Date With Dean Winchester
by FollowingButterflies
Summary: When Hollywood actor Dean Winchester gets caught up in a scandal that could threaten his career if exposed by the press his agent draws up a deal with the press. They won't expose the story if they can run a competition offering a date with Dean as the prize. Everything is fine until Dean meets the winner, Anna Milton, and her brother Castiel who Dean can't seem to stop looking at.
1. Chapter One

**Author's Note: Very loosely based off the film Win A Date With Tad Hamilton.**

* * *

**Win A Date With Dean Winchester**

**Chapter One**

Pamela's steely looking eyes glowered at Dean from across the desk as she drummed her fingers against the keypad next to her. To say that she looked annoyed was an understatement. Dean tried to give her the charming and winning smile that was plastered on buses, trains and billboards but it was no good. She pursed her lips and at that point Dean was convinced she was going to physically hurt him.

"Of all the boneheaded moves you have pulled in your time this is probably one of the stupidest." Pamela snapped. "You really had to pick now to do something like this didn't you?" She then asked looking away from Dean to furiously type something on her large computer.

"Pam-"

"Shush. I don't want you to say anything, do you hear me?" Pamela said without looking away from her screen. "I've been on the phone for three hours already and it's only ten in the morning so I really do not want to hear it Dean. I might be able to stop any publication of the offending photos but it is going to take a freaking miracle to manage. Honestly Dean, you really don't make things easy sometimes."

"Listen Pam-"

"I said 'shush' so shush." Pamela muttered. "I've only just got the phone to stop ring-" As if on cue the intercom on Pamela's phone buzzed.

"Miss Barnes, there is a reporter of The New York Post on the line wanting to speak to you." The voice of Pamela's assistant said filling the room. Dean couldn't help but give a mutual groan along with Pamela.

"Yes thank you." Pamela said closing her eyes and rubbing the ridge of her nose. She picked up the voice and tried to put on her cheeriest voice. "Yes this is Pamela Barnes" Dean then tried to drown out everything else that she was saying as he looked out the window at the New York skyline. Pamela was clearly pissed at him and he could understand that but he wasn't sure why she was _this_ pissed at him. True maybe now wasn't the right time to have done what he had done considering he'd just been nominated for several 'Best Actor' awards at teen award shows and this probably wouldn't give him the best of reputations but did Pamela really have to glare at him that much?

"Pamela?" Dean asked and Pamela raised a finger for him to give her a minute. Dean leant back in his seat and went back to staring out the window. A loud sigh from Pamela drew Dean back from staring at the skyline.

"I hate the press sometimes." Pamela muttered under her breath as she hung up her phone. "Right I think I can sort this whole mess out but it is going to take some magic to make this all go away. In the meantime can you promise me that you're not going to do anything else that will end up with your face splashed across the tabloids?"

"I can't promise you anything Pam." Dean said grinning. Pamela's frown deepened and dean realised that this was not the time to try and joke with his agent. "Ok, ok fine. I'll try. Am I excused?"

"Yes, yes you can leave now." Pamela said shaking her head as Dean rose from his seat. "Oh and Dean? The next time you decide to get a blowjob from some skinny homo in Greenwich Village either decide against it or look to see if there are any bloody photographers around that will certainly end up photographing said blowjob and selling it to every single paper in America! Now go before I decide to make your next role one in a very cheesy and sickening chick flick" Pamela snapped pointing at the door that Dean swiftly raced out of.

Well that whole thing could have gone better.

* * *

"God, I cannot believe you sometimes" Jo said laughing loudly as Dean sipped his coffee. The two of them were sat outside a café near Dean's apartment and Dean had just been going over his meeting with Pamela that morning. "You Dean Winchester are ridiculous. What were you even doing in Greenwich in the first place?" Jo asked stubbing out her cigarette in the nearest ashtray and picking up her own cup of coffee.

"I was at this party." Dean explained.

"That doesn't cover half of what I'm asking here, so spill it Winchester." Jo said rolling her eyes heavily at Dean. Dean knew exactly what Jo was asking but that would take a lot more explaining than Dean wanted to do at the moment. "Come _on_ Dean."

"I was drunk, it was a crazy party and that was that." Dean said sipping his coffee again.

"That also doesn't cover half of what I'm asking." Jo said. "I wonder why we're even friends sometimes." Jo muttered rolling her eyes.

"Because I stuck up for you all the way back in first grade when some asshole thought it was funny to push you over in the playground." Dean said.

"I punched that dickwad in the face straight after he pushed me over." Jo pointed out.

"I helped though." Dean said smirking. Jo rolled her eyes again but smirked back. "I'm a brilliant friend and you know. You wouldn't have met Al Pacino if it wasn't for me." Dean pointed out.

"That is true Winchester." Jo said. "Now you could be an even better friend by going and getting me another coffee." Jo added handing Dean her mug. Dean sighed put took Jo's mug from her and walked back into the café. For a Wednesday afternoon the place was pretty quiet and Dean appreciated that because it meant there would less of a chance for someone to recognise him and ask for an autograph. Dean didn't mind talking to his fans, in fact he really loved it sometimes but he really wasn't in the mood right now thanks to his meeting with Pamela that morning.

"Hey there, can I get two more coffees please?" Dean asked the girl behind the counter. She nodded dumbly and set about filling the mug Dean brought in with coffee. "Thanks" Dean said giving the girl a wink before handing over a couple of dollars. He waltzed back to where Jo was sitting and quickly sat back down.

"I'm still amazed you haven't given Pamela a heart attack with some of the shit you have pulled in your time. Do you remember when you were drunk on The Late Show?" Jo said reaching for her coffee and taking a liberal gulp.

"No…that could have been because I was drunk though." Dean said with a chuckle. "Still Pamela thinks she can work her magic and sort this whole thing out."

"She's going to have to be a freaking wizard to sort this out. Still, if you could explain what happened then that might help." Jo said.

"I told you Jo. I was at a party in Greenwich and got too drunk. That's all."

"Yeah sure thing Winchester. Sure thing." Jo said sounding like she didn't believe Dean one tiny bit. "I'm just going to wait to hear what Pamela has in store when it comes to damage control. Remember when you accidentally swore at that awards show and Pamela made you do that cheesy made for TV movie about the dying woman desperately seeking love?"

"Don't remind me. Sam still likes to send me YouTube links to the crappy final scene at least twice a month." Dean said shuddering at the thought of that terrible film.

* * *

It took Castiel several minutes of rummaging in his backpack to find his keys and by the time he got through the front door he wished that he had stayed in the library once he saw his twin sister Anna sat on the couch with a huge bowl of popcorn and a stack of DVDs. _Oh crap_ Castiel thought as he placed his bag on the floor. How could he have forgotten Anna's Wednesday night tradition? Every Wednesday night Anna would set up camp on the couch with popcorn and whatever crappy Dean Winchester film she felt like watching even though she'd seen them all too many times for Castiel's liking.

"Oh hey there, did you get everything at the library done?" Anna asked smiling up at her brother.

"Yes, I think so. Which mind numbingly terrible film are you burning your retinas with tonight?" Castiel said walking towards the kitchenette adjacent to their small lounge.

"Very funny Castiel." Anna said. "We can't all love terribly depressing French noir films."

"There is nothing wrong with French films." Castiel said shrugging.

"There's nothing wrong with Dean Winchester films." Anna shot back.

"There is plenty wrong with his films Anna." Castiel said as he looked into the fridge for something edible. There was not a lot of choice. Castiel sighed and went to grab the Chinese take-out menu attached to the front of the fridge. "Do you fancy a take-out?" he called out to Anna.

"You're a film snob Castiel." Anna said throwing popcorn into her mouth. "Nah, I've eaten too much take-out in the past two weeks. One of us needs to learn how to cook and by that I mean you can learn how to cook."

"Yes because we both know that is not going to happen. I hate to bring up the chocolate muffin incident of 2008 but I will have to." Castiel said.

"Point made and taken. I think Gabriel is still too traumatised to even look at a muffin." Anna snickered. "Now come and sit down, the film is about to start."

"It's not the one where he plays a depressed solider tore between his love for his country and the local village girl is it? Because that film was the worst film I have ever been forced by you to watch. That was two and a half depressing hours of my life I will never get back thanks to both you and Dean Winchester."

"I love that film! It was Oscar nominated!" Anna said sounding aghast.

"It was a terrible film Anna and I won't believe otherwise." Castiel said looking through the Chinese take-out and trying to decide what to order. "Are you sure you don't want any take-out?" he asked Anna.

"I'm sure, thanks anyway." Anna said. "You sure you don't want to sit and watch the film with me?" Anna then asked patting the space next to her on the couch.

"I'm quite sure Anna, there's only so much of Dean Winchester's bloody face I can take in one night."

"He's gorgeous and you bloody well know it Castiel!" Anna said with a chuckle. Castiel rolled his eyes and went off to order his food which he would no doubt be eating in his room to get away from his sister's adoration for Dean bloody Winchester. So while Anna sat on the couch eating too much popcorn Castiel stayed in his room eating chicken and broccoli noodles while working his way through one of the many books in his room.

* * *

On Friday morning Dean was called into Pamela's office and he knew this meeting would go one of two ways. One way would probably end up with Pamela brutally killing Dean and his blood covering her pristine office. When he got to Pamela's office, late because of the obscene amount of traffic, Pamela was sat behind her desk and tapping her foot loudly against the floor.

"Sorry I'm late Pam, the traffic was a bitch." Dean said giving Pamela and cheeky smile. Pamela rolled her eyes but didn't shout at him so Dean guessed he was forgiven. "What's this about?" Dean asked as he sat down opposite Pamela.

"I've managed to carve out a deal with the press. They won't release the photos as long as you do something good for charity and something that will smell lots of papers. I'm not going to be remotely modest about this, it was a freaking good idea and I am a God for sorting all this out." Pamela said actually smiling. Dean couldn't help but look at Pamela with confusion because he honestly couldn't see where this was going.

"So the plan is?"

"The brilliant plan Dean is that we set up a competition to win a date with you and for every entry there will be a dollar donated to some charity. It will give good publicity and hopefully the press will be sweet talked enough into not publishing those damn photos" Pamela explained.

"Wait…someone will win a date…with me?" Dean asked.

"Yes. The lucky winner will have a delightful evening out with you at some very nice restaurant and you will not act like a dickhead at all." Pamela said sounding stern in a way that meant there was no possible way that Dean could act like a dickhead.

"Why would anyone want to win a date with me?" Dean asked because if he was being perfectly honest he couldn't understand why anyone would. Sure he was a famous actor but he was sarcastic and quite blunt, they weren't normally qualities people looked for in potential dates.

"Don't be stupid Dean, you weren't voted 'Hottest Actor' by all those damn magazines for your personality." Pamela said rolling her eyes. "Now do I have your agreement to this whole thing? Because to be honest I've already gone ahead and started arranging it."

"Thanks Pamela, thanks a whole lot." Dean said with frustration. "You can't fix the winner can you? I don't want to end up with some back-water hillbilly"

"No, I cannot fix the winner Dean; you will just have to suck it up and try to be charming for one night." Pamela said. "If you screw this up I will kill you Dean and I mean it." Pamela added warningly. For that moment Dean was actually scared that his agent would kill him and she was skilled enough to make it seem like a complete accident.

* * *

Castiel was coming out of his last class of the day when the phone in his pocket buzzed several times in just a minute. Sighing to himself he pulled the phone out of his pocket and looked at the screen. Four texts from Anna and all of them had been sent barely seconds after one another. Either she was dying or something monumental had happened to her. Maybe she had finally managed to open that one cupboard in their apartment that they had never been able to open. In Castiel's eyes that was quite monumental. Castiel reached the nearest bench, sat down and read Anna's texts.

Anna Milton:

'**Win a Date With Dean Winchester' I HAVE NEVER BEEN HAPPIER THAT THIS IS GENUINE COMPETITION**

**APART FROM IF I WON**

**God I wish I was lucky**

**Do we have any jelly beans in the cupboard?**

Castiel really did not know what on earth Anna was on about and part of him really did not want to either because an excited Anna was almost as dangerous as an excited Gabriel which was in connotation with the apocalypse.

* * *

**Author's Note: I blame my sister for this because she made me watch 'Win a Date With Tad Hamilton' this afternoon and I was reading a Destiel fic at the time. Then bam, brain crack hit me and I had to start writing this even if it is terrible. If people don't hate this idea then I will carry on writing so reviews will be helpful. **


	2. Chapter Two

**Chapter Two**

"Why the hell would anyone in their right mind want to go on a date with you of all people?" Jo asked between fits of laughter on Friday night as she threw herself onto Dean's couch. Dean had originally planned on going out for the evening to some club opening that he had been invited to but Pamela had put him on lockdown and told him not to leave his apartment in case he did something to annoy the press and make them release the photos from the days before. Not wanting to stay in by himself Dean had rung Jo and now the pair of them were going to spend the night watching old films while Jo laughed at the whole competition situation that Pamela had gotten Dean into.

"That's what I asked Pamela but her reply was about as helpful as you're being right about now." Dean said grabbing two bottles of beer from the large fridge in his kitchen. He threw one of the bottles towards Jo, who caught it smoothly, then walked over to the couch and flopped down onto it next to Jo. "There is no possible way of me getting out of this shit fest is there?" he asked groaning slightly. Dean knew he had no one else to blame for this whole situation but he really had to hate Pamela and the press for a moment. Having to go on a date with some random, no doubt crazed, fan was certainly not on his list of what he wanted to do. Heck he'd rather make another terrible made for TV movie than go on this crappy date.

"Nope, probably not. That's what you get for being all slutty up in Greenwich." Jo said with a smirk before she took a swig from her beer. Dean resisted the urge to smack her. "If you end up on a date with some hillbilly straw chewer I will never stop laughing. Neither will Sam either probably. We can revel in your misery together; it'll be so much damn fun."

"Yeah, thanks for that Jo. That's so helpful, you have no idea." Dean said sarcastically as he started up the DVD. The opening credits of _Star Wars: A New Hope_ filled the large screen of his TV and made Dean feel slightly better. There was nothing that _Star Wars_ could not solve and if there was then it would probably be the end of the world.

"Oh well, you never know Dean, you could meet the love of your life thanks to this and then you can have a huge fancy wedding that's on the front cover of every shitty magazine in the country. It could even be one of those cheesy 'we're so humble' backyard weddings with stupidly huge flower arrangements and random smiling kids all over the place." Jo said with a snort. Now Dean really had to resist the urge to smack her.

"Do you just say shit like this to me to annoy me or do you really think you're funny?" Dean asked as he wondered why Jo was his best friend.

"It's a bit of both but mostly the latter. I am hilarious and there is nothing you can do to convince me otherwise." Jo said. "I'm being serious though, it would be pretty cool if you met a decent girl through this whole thing." Jo added with a shrug. Dean couldn't help but snort at that. There was no possible way this 'Win A Date' idea was going to end up with some cheesy happy ever after in which he fell for the girl who won the damn competition. "I'm just saying, it would be trippy if that happened."

"No offence Jo but that sounds like some corny storyline to a really bad film." Dean said.

"You'd probably end up starring in it as well." Jo shot back with a grin. "Then you'd end up with yet another tweeny award for starring in a crappy film."

"Give it a rest Jo, that award was three years ago and that film wasn't _that_ bad." Dean said rolling his eyes.

"It was and you know. Do you remember that you had to make that testosterone filled four hour epic war flick before Sam could even be in the same room with you without laughing?"

"I'd only just started to forget that Jo thanks so much." Dean muttered glaring at Jo who merely smirked at him. "Now can we please just watch the damn film?" Dean asked.

"You mean the one you've seen over three hundred times already?" Jo asked.

"Yes, now shut your cakehole."

"Fine but I'm still going to give you grief over this whole thing just because it's so ridiculous. Well at least until Sam comes here for the weekend then he'll give you even more grief and that will amuse me greatly." Jo said smugly.

"You're a terrible friend." Dean said shaking his head at Jo.

"I'm your only friend. Everyone else only likes you because you have a billboard in Times Square." Jo said with yet another grin as she put her feet up on Dean's coffee table.

"Really Jo?" Dean asked looking at Jo's feet. "That coffee table is hand carved oak from Scotland, please treat it with some care." He added.

"Sometimes you really sound like a fancy pants actor. What happened to the mouthy scruff from Kansas that wore too much flannel?" Jo asked rolling her eyes as she picked her feet up of the coffee table.

"He got a really nice coffee table ok?" Dean said swigging his beer.

"I worry about you sometimes; you've been living in New York for far too many years." Jo said narrowing her eyes at Dean for a moment before she turned to the TV screen and began to watch _Star Wars_. "So…can I ask about Greenwich again?" Jo asked after several minutes.

"No, no you cannot." Dean said firmly hoping that would draw an end to the conversation once and for all.

"Dang it." Jo muttered under her breath.

* * *

By the time Castiel returned home to the apartment Anna had text him another three times over general Dean Winchester related matters and Castiel knew that she would not stop once he got home. He made sure that he'd stopped off at one of the nearby coffee shops to get a large black coffee with an extra shot of espresso because he could only listen to his sister talk about some annoying actor for so long before caffeine or a bullet to the brain was needed. Castiel also made sure there would be jelly beans in the kitchen once Anna got out of her last class because, according to both Anna and Gabriel, jelly beans made everything in the world better.

Castiel was only in the apartment by himself for a few minutes before Anna came bursting through the front door throwing her bag down onto the floor and skipping into the kitchen. Without her having to say a word Castiel grabbed the beg of jelly beans from the cupboard. Anna grinned at him happily then gave him a wink.

"So have you heard?" Anna asked, her eyes shining with excitement.

"No, I've been in classes all day so I've hardly had time to look at every ten minutes unlike you." Castiel said.

"Very funny Castiel." Anna said rolling her eyes.

"So what exactly is this competition?" Castiel asked as he threw Anna the bag of jelly beans.

"It's been all over the internet this afternoon. You enter it to get a chance of winning an evening in New York with Dean Winchester plus for every entry received a dollar will be donated to a charity." Anna explained ripping open the bag of jelly beans and taking a handful. "An evening in New York with Dean Winchester!"

"Why on earth would you want to enter? It's not like you've seen all five thousand of his terrible films." Castiel said sarcastically. Anna rolled her eyes and threw a few jelly beans into her mouth. "The guy sounds like an egotistical pig to be offering a date with him as a prize."

"I think it shows he's comfortable with his fans." Anna said with a shrug.

"No, it shows that he thinks too much of himself." Castiel said. "'Win A Date With Dean Winchester' it's just so…tacky." Castiel added with a grimace.

"I'm entering anyway." Anna said resolutely. "The odds go up when you file an application."

"You're insane and you'll never win. The whole thing is probably rigged so the winner is some skinny underwear model with loose morals and large breasts." Castiel said. There was no way some actor with a huge bank balance and an even bigger ego would let himself be set up with some random crazed fan.

"I highly doubt that, there's too much publicity on this thing already as it is and it was only announced this morning." Anna explained.

"I just think it's pretty silly to be going crazy over some stupid competition."

"You're sounding like a spoil sport and I hate to remind you of the time you were eight and you went on a silent hunger strike for a week when you didn't win that competition to visit the _Harry Potter _film set." Anna said poking Castiel in the chest.

"That was an emotional time." Castiel said narrowing his eyes at his sister.

"whatever, you're a nerd" Anna said rolling her eyes and throwing more jelly beans into her mouth. "Anyway, what are you planning on doing tonight? There's a party at my friend Ruby's dorm. I'm heading over there in about an hour; do you want to come with me?" Anna asked.

"No thanks, I have a paper due on Monday and a few books that I've been meaning to read for ages." Castiel said. He wasn't going to mention to his sister that Ruby drove him insane and if he could get away with not spending time around her then he was very happy.

"You are getting to be a real introvert. We only have a few months left at college; you should let your hair down…metaphorically." Anna said. Castiel couldn't help but shrug at his sister. He wasn't one for going out and partying, he preferred staying in and reading a good book or watching a film (that didn't star Dean bloody Winchester). Sure Anna liked to stay in watching films with him but she also had an active social life at college and spent a lot of time at parties that Castiel normally avoided like the plague. He was happy being by himself a lot of the time. "Fine" Anna said seeing Castiel's firm looking stare directed towards her. "But I am going to drag you out one of the nights. You haven't lived at college until there is incriminating photographic evidence of you doing something wrong, illegal or drunken."

"Or in Gabriel's case it's all three." Castiel said smile creeping on his face despite his disapproval of his younger brother's partying habits.

"He really doesn't count yet, he's still in high school." Anna said.

"That should be more disconcerting than it actually is." Castiel said more to himself but Anna nodded in agreement. "You go off out, at least I will have the TV to myself for a night."

"Oh that reminds me! _Cupcake Wars_ in on tonight, will you record it for me?" Anna asked and Castiel honestly felt like hitting his head on the nearest cupboard door. Anna really did have some terrible taste in television shows sometimes.

* * *

Once Anna was out the house Castiel grabbed his laptop, his notes from his English Literature class and a few books he was planning on reading and placed them all on the couch. Before he went to the kitchenette to grab a drink he turned the TV on. Once he was rummaging through the fridge he heard the low hum of the TV.

"Coming up next on E! From Rags to Riches: The Dean Winchester story." The announcer said and Castiel rolled his eyes. Honestly there are no escaping sometimes. Grabbing a bottle of beer Castiel went back towards the couch and made to change the channel quickly just as Dean's face popped up on the screen.

"Yeah, growing up Kansas then moving to New York was a huge shock for me. I was just this small town kid who somehow landed on his feet in this huge city and managed to get some damn good acting gigs. It's all pretty crazy." Dean Winchester on the screen was saying as he grinned at the reporter. The smile was so arrogant looking it pissed Castiel off instantly. How could Anna like that douchebag and more importantly how did she manage to make Castiel go with her to every single one of Dean's terrible films?

"I don't think so." Castiel muttered changing the channel to a random music channel that wouldn't distract him while he wrote his English Literature paper. If he could get through one evening without having to see Dean Winchester's face he'd be very happy.

* * *

Dean was leaving his apartment and pulling on his leather jacket when he heard his phone ringing from his back pocket. Pulling it out he grinned when he saw his brother's name appear on the screen.

"Hey there Sasquatch, how's the view from where you are?" Dean asked.

"Ok so you're being pimped out to some poor member of the public and you don't bother to tell me about it?" Sam said sounding annoyed.

"Fuck, did Jo text you?" Dean asked. He was going to kill Jo for this.

"No, I had to find out by watching E! News of all things." Sam said sounding seriously pissed off.

"Since when did you watch E! News?" Dean asked. Sam was more of a documentary or _Law and Order_ kind of guy.

"Jess likes to watch it."

"Ah yes, the girlfriend." Dean said snickering. "How are you two love birds?" Dean asked.

"We're fine Dean, thanks for the interest."

"The fact I still haven't met the girl you've been dating for six months is most annoying. Are you convinced she'd dump you for the more attractive, richer and talented brother?" Dean said knowing exactly who to annoy his brother.

"You're an ass." Sam said and Dean was sure he was giving Dean his famous 'bitch face' down the phone. "Jess really likes me so you have no chance whatsoever. Anyway that's not the point of this whole conversation. What the hell is this whole 'Win A Date' thing about?"

"It's some shitty idea Pamela and the press had. It's supposed to be good for my reputation" Dean said rolling his eyes.

"Why the hell would anyone want a date with you?" Sam asked.

"Thanks for that bitch." Dean said. "And besides I'm not being pimped out."

"You're donating money to charity in exchange for a date; I'd class it as you being pimped out. Oh you actors and your crazy ways…" Sam said chuckling.

"I swear I sometimes hate you more than I hate Jo." Dean

"No you don't, you love me really you jerk." Sam said with a chuckle "Hey what happens if you end up on a date with some random hillbilly girl?" Sam then asked.

"It worries me that you, Jo and I have all asked that same question." Dean said

"We clearly have brilliant priorities." Sam said. "So what are you up to now?"

"I'm about to get a cab because I have meeting with a director about this new film this afternoon and I'll no doubt have yet another glorious meeting with Pamela over me being 'pimped out'. What about you, are you busy doing future lawyer stuff?"

"Yeah sure, the classes are good and everything. It'll be good to come to New York and catch up with you soon though." Sam said and Dean closed his eyes for a moment. He hated being so far away from his brother but being in New York was the best thing for his career and that meant that he could easily pay for Sam's tuition to Stanford. He just wished that he got to see Sam more often. It had been nearly two months since they had last seen each other so Sam coming to New York was certainly something Dean was looking forward to. Just spending time with his little brother would be a great thing.

"It'll be good to see you too Sammy, you can hit up Dylan's Candy Bar and throw up again." Dean said smirking at the memory of watching Sam acting like a small child in the confectionery store. Dean punched the button of his elevator and waited for the elevator to reach the top floor.

"Dean! That was once and it was more to do with the six beers that Jo gave me." Sam said in protest.

"The nine chocolate bars probably didn't help either Sammy." Dean pointed out smirking as the elevator arrived. "Now I've got to catch a cab and head to this meeting, I'll ring you later."

"Whatever Vivian Ward, you go off and have a good day." Sam said snorting.

"Did you just refer to me as that character from _Pretty Woman_?" Dean asked frowning. His brother had clearly been watching far too many films with that girlfriend of his and some really bad and cheesy films at that. Nothing involving Richard Gere was a good thing as far as Dean was concerned.

"The fact that you know which film I was referencing proves far too much Dean, enjoy your meeting jerk." Sam said making Dean roll his eyes as he walked into the elevator and pressed the button for the lobby.

"Yeah see you soon bitch." Dean said before he hung up the phone. Glad to know that everyone he knew was getting a kick out of this while competition crap fest he'd gotten himself into. Damn Greenwich…

* * *

**Author's Note: I just want to say a huge thank you to the amount of reviews and follows this story has gotten when I've only just posted one (well now two) chapter. This whole fic purely came from watching the film Win A Date… with my sister the other day (for a seven year old she has a very broad taste in cheesy romantic films which I blame my mother for) and I just want to say a huge thank you to everyone reading and enjoying the fic!**

**Also there is nothing wrong with **_**Cupcake Wars**_**, that show is actually addictive like **_**Cake Boss**_**…I watch too many food related shows. **


	3. Chapter Three

**Chapter Three**

Sunlight was streaming through the ceiling to floor windows and it filled the room so much that Dean thought he was going to headache anytime soon. He was sat in a large leather chair watching as several people had a conversation about him that he had no say what so ever. This was nothing surprising though, he'd been to casting meetings before and he would certainly have many more in the future.

"So Dean…" a tall woman said crossing her legs and leaning forwards towards Dean with a smile on her lips. "We loved your work in _The Extraction Point_. It was a very powerful film and you've got a good, strong body of work. We're just concerned about your roles in films that have been targeted towards the teen demographic. You've recently been nominated for several awards at teen based award shows so we don't want to cast you and have people think you're just some pretty boy actor hired to draw in the crowds." The woman added looking Dean up and down in a way that made him feel very uncomfortable.

"Thankfully you did make _The Extraction Point_ which does help." The director's assistant said quickly smiling at Dean. Dean tried to smile back but he could really feel a tension headache forming. Yeah was not enough coffee to make this headache go away. Damn Pamela for convincing him to make those cheesy films. True they had paid well so Dean was able to keep Sam at Stanford and living in a great apartment as well as keeping Ellen, Bobby and Jo comfortable but when it came to doing a film he really wanted to they tended to bite him on the freaking ass just like it was doing now.

"I understand, though I do feel as though it helps show off my range and prove that I can reach many demographics." Dean said parroting the line Pamela had given him time and time again. The assistant smiled then nodded in agreement. Thank Jesus for that.

"That is very true Dean, thank you so much for coming in to speak to us today. We're really excited about this project and knowing that you are as well is very positive for us. We'll get back to you about the role. Your agent Pamela Barnes should hear back within the next few weeks." The assistant said smiling. Well it wasn't a 'no' but it wasn't a 'yes' either. Dean shook the hand of everyone in the room and swiftly left to call Pamela and beg her to convince the casting people that he deserved this role.

* * *

"So the contest is going really well so far, we've already raised ten thousand dollars so you should be pretty darn pleased." Pamela said when she answered the phone. Ten thousand dollars? It had been _two days_ how could they have raised ten thousand dollars already? Clearly there were too many people in the country that thought going on a date with Dean was the greatest thing in the world.

"That's great Pamela but could we focus on something else please?" Dean asked. He walked out the building and pulled his sunglasses out of his pocket to shield his eyes from the sun and to try and avoid getting a headache.

"Dean this contest and the publicity gained from it will be important." Pamela said.

"Yes but there are more important things to talk about, like the meeting I just had with the casting people of _Diversion_." Dean said reaching the end of the sidewalk and signalling for a cab.

"Yes of course, what exactly did they say to you? They're calling me later on but it would be good to hear about it from you." Pamela asked.

"They said that they liked my work in _The Extraction Point _but they think that those shitty teen film roles you got me might hinder the casting process. Can you please convince them that I want this role? It sounds like a great film Pamela and I need this role. The script is really good and it's got a real buzz around it already." Dean explained to Pamela. A cab stopped near him and Dean quickly climbed in. He gave the cab driver his address then settled into the seat.

"I understand Dean and I'll get on at them about it but at the moment can you make sure you're putting enough publicity on the 'Win A Date' competition. It will be good for your reputation and also it will get the press to back off with those damn photos." Pamela said.

"Yes Pamela" Dean growled. This fucking 'Win A Date' thing was going to seriously kick him the ass by the time the whole thing was over. Dean hung up the phone and shoved it into his back pocket with irritation. Once again Dean was cursing goddamn Greenwich for getting him into this mess. He thought about calling Sam to vent his annoyance but that wouldn't really help as he would probably have to explain the whole reason behind the 'Win A Date' bullshit and he really did not want to get into that right now.

The whole thing was insane and Dean really was cursing Pamela for agreeing to the competition. It was going to be a disaster, it was going to be the most awkward night of Dean's life and he knew that. The winner would most likely be some insane fan that wouldn't be able to say two words before giggling inanely or worse, crying. Things like that had happened before and it had just made Dean feel like he was a piece of famous meat, it was like no one really knew who he was apart from Dean Winchester the actor. Dean Winchester the Hollywood movie star and nothing else.

After twenty minutes the cab stopped outside Dean's building and Dean handed the guy the fare before climbing out the cab. He looked up at the building where he'd lived in the penthouse for the past year and half and sighed deeply. This was his home and yet sometimes it felt like someone else's. It wasn't the house he'd grown up, heck it wasn't even a freaking house really just a flat space with a fair few rooms. It only ever felt like a home when it was full of the people he loved like Jo, Sam, Ellen or Bobby. When they were in the apartment it felt less empty and for time Dean could pretend that he was just regular Dean back in Kansas.

Dean rode up the elevator rubbing his temples to try and get rid of his headache that had indeed appeared. When he got to the penthouse he let himself in and threw his phone and keys onto the nearest table. For a moment he thought about ringing Jo to complain about the casting meeting but then realised she was at work and she'd get in trouble if she took personal calls. Once again he thought about ringing Sam but talking to his brother would make him go into an even funk than he already felt in.

"Fucking hell, pull yourself together Winchester." Dean muttered to himself before he went over to his large bookcase full of DVDs. When in doubt of yourself or your life turn to escapist cinema. Preferably with a Death Star, Han Solo and The Force. That was the rule Dean had lived by since he was a child and he would probably live by that rule for the rest of his life.

* * *

Icy rain hammered at the windows and the heat from inside a café made the windows steam up, shielding everyone inside from the view of the dreadful weather. Inside the air was filled with the warming and powerful smell of fresh coffee and pastries.

"Americano with hazelnut, cappuccino with cinnamon and a plain Americano?" a barista called out in a very bored sounding voice.

"Oh yeah that's us!" Ruby said leaping to her feet and going to pick up the coffee. "So, has Anna driven you completely insane about this whole 'Win A Date With Mr Fine Ass' competition already?" Ruby asked when she came back to the table and sat down opposite Castiel as he reached for the cup of coffee. Castiel, Ruby and Anna were all sat in the café near the University of Chicago campus sheltering from the terrible weather as they all had a free afternoon.

"Oh please Ruby, I'm hardly driving you insane about it." Anna said. "I've mentioned it once."

"Once a minute is more like it." Ruby said.

"Of course Ruby, of course. It's not like you don't happily ogle every photo and clip of Dean Winchester that you can get your hands on" Anna said sound triumphant.

"Meh, I'm more of a Dr Sexy kind of girl." Ruby said shrugging.

"God I hate that show." Castiel muttered under his breath.

"You would hate that show." Ruby said narrowing her eyes at Castiel for a moment. "But back to my question…is Anna driving you insane over Dean Winchester yet?"

"I wish we could go one day without that name being mentioned. It really would make my life a lot more fulfilling and pleasing." Castiel sighed.

"Answer the question Milton." Ruby said huffing slightly.

"I'm just filtering it all out if I'm being perfectly honest. I've had to sit through every single one of the guy's movies; the thought of my sister applying to win a date with him is just too much." Castiel said grimacing. He'd been dragged to the cinema far too many times by Anna to see the latest Dean Winchester film; that was probably one of the downfalls of being best friends with your twin sister.

"I am sat right here and I can hear you." Anna said poking Castiel in the arm.

"Good" Castiel said with a quick smirk at his sister. "Hopefully this means that you won't enter the competition and I won't lose all respect I have for my sister." He added before he sipped more of his coffee.

"Too late, I saw her send off her entry this morning." Ruby said throwing a piece of bagel into her mouth.

"Jesus Christ, Anna I'm replacing you with Gabriel as my favourite sibling now." Castiel said to Anna who just rolled her eyes.

"Yeah and I'll give that a week before Gabriel says something inappropriate and you back to viewing him as an annoying puppy." Anna said with a loud chuckle.

"You might have a point there." Castiel said remembering far too many times when Gabriel had annoyed him to the point of insanity.

"Oh Gabriel, that kid slays me sometimes." Ruby said smiling at many memories of when Gabriel had travelled to Chicago and flirted mercilessly with Ruby. "When's the mischief maker coming next anyway?" she asked.

"God knows, he's never actually tells us when he's coming here. He just pops up like some annoying gnome." Anna said taking a large gulp of her coffee.

"I think he's funny." Ruby said with a shrug.

"That'd because you see him several times a year. We're related to him and have to put up with him for seventeen years already. That's seventeen year too long actually." Castiel said. Ruby chuckled with a shake of her and went back to sipping her coffee. She and Anna chatted about their days while Castiel zoned out for several minutes. His morning classes had been long and tiring and he had yet another paper to write on a novel they were reading in his class so it looked like that was what he was going to be busy with over the next week until it was finished and perfected. Castiel zoned back into the conversation between Anna and Ruby, he heard Dean Winchester's name then swiftly zoned back out again. There really was no escaping that talentless moron sometimes.

"-crazy, right Cassie?"

"What?" Castiel asked looking up at Ruby who was looking at him expectantly.

"I said Anna's crazy for entering this competition and she's just going to look like a crazed fan." Ruby said.

"I'm not agreeing with you on anything because I have to live with her, she might take anything I say out on my clothing like the time she turned my favourite shirt pink."

"That was an accident I promise you that." Anna protested.

"Yes, of course it was." Castiel said rolling his eyes as he silently mourned the loss of his favourite shirt yet again

Ruby sat back watching Castiel and Anna bicker for a moment before she said "You two make me glad that I'm an only child." Anna rolled her eyes and went back to drinking her coffee without saying another word. "Thinking about it I would make an excellent sister."

"I think you misunderstand the definition of 'excellent'. It doesn't mean to torture and ruin the life of a sibling." Castiel said. Pain shot up his shin as Ruby gave him a swift kick under the table. "That hurt."

"Good because it was meant to." Ruby said "Now stop being such an ass to me all the time." She added with a pout of her lips.

"I just cannot help it sometimes Ruby, you make it too easy." Castiel said with a snicker.

Ruby gave him the finger before saying "This is why you don't have any friends"

"I have friends." Castiel said in objection.

"Anna doesn't count because she's your sister." Ruby quickly replied. She might have had a point there then. It wasn't that Castiel was antisocial per say it was just that he didn't get along with most people as they sometimes found him standoffish. He got on with some people just fine but most people…well most people confused him sometimes. "Face it; you're an ass to most people."

"You say that like it's a bad thing" Castiel said grinning at Ruby's bitch face.

"Anna…I hate your brother." Ruby said turning to Anna with a frown.

"Shush" Anna said raising a hand to silence Ruby "I'm enjoying my coffee too much to think about your hatred of my brother."

"Now I hate you a bit as well." Ruby said as she glowered at Anna who merely smirked back at her.

"Take it up when I'm not drinking cappuccino." Anna said closing her eyes with a smug smile as she gripped her large mug of coffee. Ruby rolled eyes heavily and went back to tearing up her bagel and throwing pieces into her mouth.

**Author's Note: Thanks to everyone currently reading this and giving reviews and such. It really means a lot to me and I'm glad you like the story so far. Sorry if this seems like a bit of a filler chapter but we're getting into the story a bit from now on.**


	4. Chapter Four

**Chapter Four**

_One Month Later_

Steamed rose from a disposable coffee cup as Dean placed sunglasses over his eyes to shield him from the harsh sunlight. Taking a generous gulp of the hot liquid Dean hurried down the street towards Jo's apartment. She had the day off from work and so they were planning a day of doing simply nothing but sitting on her sofa, drinking beer and watching films. Dean was in a pretty decent mood, he'd had a meeting with a director the day before about a small indie film that wasn't normally the kind of film Pamela gave him but the script had been really strong and the main character had interested Dean. He wasn't as passionate about it as he was with _Diversion_ but it was still a project he was interested in. Dean was nearing Jo's apartment when he heard his phone ringing from his back pocket and Pamela's name flashed up on the screen.

"Dean, my favourite little client! I have very good news for you!" Pamela cried as soon as Dean answered his shrilly ringing phone.

"The casting people from _Diversion_ finally got back to you about the role?" Dean asked hopefully even though he hated how eager he sounded over the role.

"Oh no sweetie, they're taking a breath at the moment" Pamela said flippantly.

"Wait…what? They're taking a breath? What the hell does that mean?" Dean asked.

"It means that they're taking some time out when it comes to casting, they're thinking things over."

"So why are you calling me?" Dean asked sighing because waiting around for this fucking role was actually killing him. All he wanted to do was to get this damn part and yet now they were 'taking a breath'…taking a fucking breath. It was brutal.

"Because the competition is over." Pamela explained sounding far too excited.

"What competition?" Dean asked dumbly wondering what the hell Pamela was on about. "Wait…the 'Win A Date' thing? You mean it's been cancelled? Thank Jesus for that because I really did not-"

"Dean it's not been cancelled. It's over because they're got a winner." Pamela said sounding tired and frustrated.

"Oh...oh right…um…do I find out who it is?" Dean asked dumbly because really how the hell was he supposed to know how to react to something like this? Once again Dean prayed that the winner wasn't some hillbilly crazy stalker fan who would trick him into signing a marriage contract or some bullshit like that.

"Apparently it's a girl from Illinois called Anna Milton. I'll find more out about her soon but she'll be coming to New York in two weeks for the date." Pamela explained. Well at least the winner wasn't a hillbilly. "Now I've got to go, I've got a meeting this afternoon but remember that this is a good thing you've received a lot of positive press from this and you've raised a hell of a lot of money for charity." Pamela said. "I'll call you if I hear anything from the _Diversion_ people."

"Thanks Pamela." Dean said before Pamela hung up the phone. Now he really needed that beer with Jo. He hurried down the street until he came to Jo's building and rang the buzzer. Jo quickly buzzed him and had the door open waiting for him when Dean got to her apartment.

"Whoa there Winchester that's some scowl you got there. What's up with you?" Jo asked when she saw Dean.

"Pamela rang me, the contest is over." Dean explained.

"They actually found someone to go on that crappy date with you?" Jo asked snorting. Dean rolled his eyes and when he walked into Jo's apartment he threw himself onto her couch with frustration. "So who's the lucky, _lucky_ girl?" Jo asked with a grin.

"Some girl named Anna Milton from Illinois."

"Well at least you know she's not some straw chewing hillbilly." Jo said throwing a bottle of beer at Dean. "Isn't that what you were afraid of?"

"Yeah but she could still be insane." Dean pointed out.

"Well that's obvious; no sane person would want to go on a date with you." Jo said with a smirk.

"Thanks for that Jo." Dean said with a voice dripping in sarcasm.

"You're welcome." Jo said sweetly. "Oh come Dean, it's not going to be that bad is it? You've been on dates before when you didn't really like the person and this probably won't be any different. Just smile, be nice to her and you'll will probably make the girl's life complete. Most girls dream about dating a movie star and you'll be making a dream come true. Stop being such a grump over it."

"It's going to be the most awkward evening of my life Jo." Dean groaned.

"Clearly you're forgetting our junior prom back in high school" Jo said with a shudder at the memory.

"Oh yeah…ok it will the second most awkward evening of my life."

"Or it could be semi-decent and this girl from Illinois could be pretty damn cool." Jo said. She was trying to sound helpful and Dean had hand it to her that it was slightly working. The evening would give him should good publicity and get Pamela off his back about Greenwich. "Now this is my first day off all week so I'm going to enjoy sitting on the couch and doing fuck all today."

"That sounds good to me." Dean said grinning at his best friend. The pair of them settled on the couch with a good DVD and several bottles of beer. Dean thanked God that Jo had the same taste in his as him so there was no debate on what to watch. They were halfway through one film when Jo piped up again.

"If you get married to this girl then can I be a bridesmaid?" Jo asked digging Dean in the side with her elbow. "Well as long as I don't have to wear some tacky dress." She added.

"Shut up Jo." Dean said rolling his eyes. "This whole shitty competition is really not funny" Dean said with a grumble.

"Oh cheer up Winchester." Jo snapped sounding annoyed. Dean gave her an apologetic look which seemed to satisfy her. "So…when is this date then?" Jo asked.

"It's in two weeks."

"Aww, that's just enough time to pick out the perfect outfit and get all pampered." Jo said with a snicker.

"Jo…" Dean said warningly.

"I know, I know…shut up." Jo said holding her hands up in surrender.

"Thank you." Dean said hoping that Jo would indeed keep quiet over this for the next two weeks otherwise Dean would end up going completely insane.

* * *

Shoving his copy of _Brighton Rock_ back into his messenger bag Castiel hurried across the campus to the bike racks where his battered old bike was chained up. His lecture had been long and full of overly opinionated people that really did not understand half of the context in _Brighton Rock_. Groaning to himself Castiel unchained his bike and thought lovingly of the several mugs of coffee he was going to consume once he got back to the apartment. He was also going to happily sit and work his way through a whole box set of a show he'd been meaning to watch for a while. If he beat Anna back home then he would have control over the DVD player and he wouldn't have to watch four Dean Winchester films in a row or worse…if there was anything worse than that. Mounting his bike Castiel began to peddle away from the campus and back towards home.

The ride wasn't long and Castiel always enjoyed it, unless it was raining. The ride always gave Castiel time to think and generally contemplate his existence in the world though what good that did in the long run Castiel did not know. Nevertheless he enjoyed cycling around Chicago even if it was sometimes lethal during the rush hour traffic. Actually now that he thought about it the traffic this evening was quite bad.

Castiel slowed down about a block away from the apartment because the road was full of what looked like new vans. Maybe the crazy cat lady from down the road had gone insane and shot the hobo that threw tai take-out at her cats. Castiel dismounted his bike and hurried down the street until he reached the start of his street. At least ten news vans were crowded out outside his building so clearly crazy cat lady had not shot tai take-out hobo. Castiel had to admit that he was slightly disappointed by that fact.

He chained up his bike and pushed his way through the reporters to get to the building and could hardly hear whatever anyone of them was saying as it was so quick. Castiel unlocked the door quickly and raced into the apartment building, hurrying upstairs until he got to his apartment. He could hear the television on from inside so Anna was obviously at home already. There goes Castiel's night in a with a box set.

"Anna? Anna why is there every reporter in Illinois standing outside our apartment building?" Castiel asked as he opened the apartment door and walked inside. Out of the corner of his eye he saw something pale and red hurtling towards him.

"Castiel!" Anna cried running up to Castiel, grabbing onto his arms and looking more excited than the time there was an all-day marathon of _Cake Boss_ on the Food Network. Castiel was very tempted to grab his bike and get away from the apartment as quickly as humanly possible. "Castiel I won, I _won_." Anna said grinning from ear to ear.

"Won what?" Castiel asked wondering what the hell Anna was talking about. Maybe she'd won a year's supply of Folgers Coffee again. That was a good year…

"_The_ competition! The 'Win A Date With Dean Winchester' competition! I won! I'm going to New York and meeting Dean Winchester. Dean Winchester! _The_ Dean!" Anna cried. Oh dear God… "I'm going to New York!" Anna screamed.

"I think I just went deaf." Castiel said sighing. He really hoped he was dreaming. He would wake up and it would be the morning all over again. He thought about pinching himself for a moment until Anna hit him on the arm.

"Aren't you listening to me? I won this freaking competition Castiel! I'm going to New York!" Anna said still grinning from ear to ear. Castiel tried to think of how long Anna would go on about this and realised she would probably still be talking about it by the time they turned thirty. Castiel wondered if he could convince Ruby to let Anna live with her to save Castiel the endless, _endless_ talk about Dean Winchester.

"That's…that's…good?" Castiel said knowing full well that he sounded very doubtful indeed.

"I need to Ruby to successfully react to this to its full potential don't I?" Anna asked rolling her eyes at Castiel. "Please can you be happy for me, please?"

"I am happy." Castiel said not sounding at all convincing and he knew it. Anna sighed loudly thus proving that Castiel had not been at all convincing. "Ok fine, I'm happy for you but less than happy for me who will now have to hear even more about Dean Winchester than before…if that is even possible. Just tell me when you're going. I can arrange a trip back home and see if Gabriel's hijinks and shenanigans are enough to make me forget that my sister will be on a date with America's highest paid moron." Castiel said. Anna tried to give Castiel a smile but she just looked away and suddenly looked very nervous. That was not a good sign at all. "What?" Castiel asked suddenly feeling very nervous himself.

"Castiel…" Anna sang pleasantly. Yes, this was not a good sign in the slightest.

"No." Castiel said quickly and firmly.

"You don't even know what I'm about to say."

"The way you're saying it implies that you're about to ask me something that I really don't want to hear or do so I am saving myself from it now by saying 'no'. It's a highly useful defence system I found actually worked against Gabriel."

"Well it doesn't work against me. Now Castiel-"

"You're going to ask me to do something I don't want to do, I know it."

"No I'm not…ok maybe I am. The competition winner gets to go to New York for the weekend and they get to take someone with them-"

Castiel was very uncompromising when he said "No."

"I didn't even finish my sentence" Anna pointed out.

"You didn't even have to because I said no, take Ruby with you instead." Castiel said almost pleadingly.

"Even though I love her you know Ruby will just be annoying" Anna said.

"Take someone else then…anyone else." Castiel begged.

"I don't want to take anyone else with me. Please Castiel, please come with me."

"What can I do to convince you that there is no possible way that I am going to New York with you?" Castiel asked even though he knew full well that once she got something into her head there was no way Anna was going to back down. Castiel was going to New York and there was nothing he could to stop that.

"Nothing what so ever. My mind is already made up" Anna said stubbornly.

"Really?" Castiel asked but he knew at this point there was no arguing with Anna. That was one of the things she had leant growing up with Gabriel.

"Really. You're coming with me and that's final." Anna said triumphantly.

"How long do I have to be there for?" Castiel asked sullenly.

"Two days."

"If I go, and I said '_if_' then you're not allowed to mention Dean Winchester once unless I ask you a question relating to the talentless ass." Castiel said trying to sound somewhat in charge of the conversation. "Ok?" he asked. Anna nodded her head and gave Castiel a smug smile. "I hate you so much right now; you don't even understand how much I despise you."

"I don't care because I'm going to New York and going on a date with Dean Winchester. My life has been made." Anna said smugly.

"I'm going to regret coming with you to New York for the rest of _my_ life." Castiel said trying to think of any possible way the trip could be fun. Maybe it would be fun if he threw himself of the statue of liberty…or maybe he could go to the Strand bookstore and spend far too much money on books. That might be a safer option than launching himself off a national treasure.

* * *

Instead of his night on the couch Castiel stayed in his room and watched a box set on his laptop. Anna was too busy sitting on the couch and talking to Ruby on the phone about going to New York. Sometime during the night she rang Gabriel and spent nearly an hour talking about the date and New York. Gabriel loved Dean Winchester's films almost as much as Anna (Castiel was convinced that he was the only one in the family with any taste) so knowing that his sister was going to be going on a date with Dean Winchester probably sent Gabriel over the edge of excitement. Castiel was going to need a miracle to get through this whole thing.

Castiel was just starting another episode when there was a knock on his door. He removed his headphones and called Anna in because it was obvious it was her. When she walked in there was a huge smile on her face and the phone in her hand.

"Do you want to talk to Gabriel?" She asked.

"Has he killed anyone?" Castiel asked because that was normally the first question anyone asked when talking about Gabriel.

"Nope, no one has been murdered or impregnated by Gabriel since the last time we spoke to him." Anna said giving Castiel a knowing smile.

"Go on then." Castiel said holding out his hand so Anna could pass him the phone. "Hello Gabriel." He said once Anna had handed him the phone.

"Well hello big brother. Aren't you _thrilled_ for our darling sister?" Gabriel asked in his normal voice that always sounded like a mix of roguish and mocking.

"Ecstatic" Castiel said with a voice heavy in sarcasm.

"Oh stop being such a sour-puss dear big brother. Our lovely sister is going to be up close and personal with a certain Mr Winchester, I for one am very excited for her." Gabriel said with a chuckle.

"Yes because the greatest experience of anyone's life is obviously meeting Dean Winchester." Castiel said sarcastically. Anna gave him a look and then rolled her eyes heavily. "I'm very happy for her Gabriel, now was there anything else you wanted to talk about or was Dean Winchester the only subject of conversation you were interested in?" Castiel asked.

"Well the only thing you ever really talk about is depressing books and dull films so that seemed like the only good subject." Gabriel said.

"Thank you for that Gabriel." Castiel said unable to hide the sarcasm in his voice.

"Oh God, put me back on the phone with Anna. She's less sarcastic than you." Gabriel said and so Castiel handed the phone back to Anna. She rolled her eyes at Castiel yet again and walked out his room talking to Gabriel. Castiel pressed play on his laptop and went back to watching the episode he'd been watching before Anna had come into his room. He sensed he was going to be spending a lot of time in his room, hiding from this whole 'Win A Date' situation for the next two weeks purely to save his sanity.

* * *

Two weeks went by far too quickly for Dean's liking. He'd tried to keep himself preoccupied with meetings, an interview with _Good Morning New York_ and several nights out with Jo or friends he'd made from past film over the past two weeks so he didn't have to think about the date too much. Sadly before he knew it he was waking up on the Saturday of the 'Win A Date' date and pretty much dreading the whole evening though he knew under pain of death that he had to be ridiculously charming and polite to this Anna Milton girl or the press, and more importantly Pamela, would butcher him.

Dean pulled himself out of bed despite wanting to stay asleep all day. Maybe he could distract himself enough today so he wouldn't think about how much he didn't want to go on this damn date tonight. It wasn't that he was a complete asshole and didn't want to meet one of his fans; it was more because he knew the night would probably be awkward as fuck. Hopefully nothing else would go wrong today otherwise Dean knew he'd be questioning his sanity soon enough.

When he heard a loud clatter in the kitchen Dean stopped. Another clatter came a few seconds later and Dean knew he'd have to act quickly. He grabbed the nearest object, a large silver picture frame holding a photo of Dean, Jo, Sam, Bobby and Ellen that was taken three years before, and he crept through the apartment until he came to the source of the noise. Crouching behind the nearest door Dean breathed in deeply and prayed that whoever was in the apartment wasn't carrying a weapon. Well the best option was that it was Jo but she was at work until three so there was no chance it was her. Dean was thankful of all the fights he had gotten into when he was younger now so he would at least stand a chance against whoever was rummaging around in his kitchen. Taking a deep breath Dean made sure he had a firm grasp on the photo frame then raced into the kitchen as quickly as he could. He was about to hit whoever it was in there when yelled loudly.

"Holy shit Dean! What the hell are you doing?" Sam cried dropping a coffee mug on the floor.

"Fucking hell Sammy!" Dean yelled groaning loudly.

"Were you about the hit me with a photo frame?" Sam asked glaring at the heavy frame in Dean's hand.

"I thought you are a burglar or some shit like that! What are you doing here? How did you even get in?" Dean asked throwing the picture frame onto the kitchen table

"You gave me a key don't you remember?" Sam asked.

"Fucking hell Sam…" Dean muttered. "Next time bitch can you warn me that you're coming over?"

"Yeah sure thing jerk. Now come, did you really think I was going to miss out on this stupid 'Win A Date' thing? I got a plane here and thought I'd witness the hilarity." Sam said picking up the coffee mug he'd dropped. Dean resisted the urge to give his brother a swift kick.

"You're about as helpful as Jo." Dean muttered grabbing a hooded jumper from his couch and pulling it on over his head. "You can make yourself useful and make me a coffee…without breaking anything."

"Ok, try not to attack me a frame in the meantime you ass." Sam muttered with a grumble.

"Yeah yeah, tell it to someone you didn't just freak out." Dean said sitting himself down at the kitchen table and looking over his brother. Sammy looked exactly the same as the last time he'd seen him apart from maybe he was an inch taller but that was nothing new as Sammy never stopped growing. He also hasn't grown out those stupid bangs that made him look about fourteen yet despite the teasing Jo and Dean had given him since he was actually fourteen. "So bitch face, how's smart person school treating you?" Dean asked. Sam launched into a long ass story about his classes and his friends and he didn't shut up for nearly forty minutes once he got onto the subject on his girlfriend Jessica. "Am I ever going to meet this girl?" Dean asked as he drank the third coffee Sam had made for him.

"Let me think…no. Jess is way too nice to ever meet you. I really like this girl Dean, she's smart and funny and totally beautiful. If you meet her then you'll end up telling her crappy and embarrassing things about me."

"I'm your big brother, that's my job." Dean said giving his brother a wink. Sam sighed loudly and gave him the ever famous Sam Winchester 'bitch face'

"You're an asshole Dean." Sam said.

"No, I'm awesome. Now you've bored me with tales of Stanford for the past hour and a half and I am starving. How about we grab some breakfast and you tell me any story that doesn't involve a lecture about law." Dean said grinning now because at least he could spend the day with his baby brother before the most awkward evening of his life…after junior prom.

* * *

The flight from Chicago to New York hadn't technically been long but to Castiel it had felt like the ride had lasted a lifetime. Castiel had tried to distract himself by re-reading _Slaughter House Five_ for the sixth time but Anna's constant rambling had driven him nearly up the wall. Thank the Lord they were in first class with the free champagne and decent leg room because if they had been in coach class Castiel might have locked himself in the cramped aeroplane toilets just so he could have five minutes alone to himself.

When they landed at JFK the pair were met by a limousine and a surly looking guy that went by the name of Chuck. Apparently he worked for Pamela Barnes, the woman who had arranged the whole competition. The smile on Anna's face was so infectious that even though Castiel had barely slept he couldn't help but give his sister a small smile. Heck, he may have been dragged to New York so his sister could go on a date with Dean Winchester he was still in New York. He was going to try and enjoy this weekend even if a large apart of the weekend involved Dean freaking Winchester. Well at least Castiel wasn't the one going on a date with him.

They arrived outside their hotel and Chuck led them inside. Both Castiel and Anna's mouths dropped at the sheer luxury of the hotel's lobby. Castiel had never been inside somewhere so damn extravagant and looking down at his ratty converse made him think that he should have dressed up in more than a shirt, University of Chicago jumper and a pair of worn jeans. Then again that would involve owning clothes that didn't look like he'd been wearing them for the past four years.

"You're in the penthouse suite Miss Milton, Mr Milton." Chuck explained handing Anna a room key then Castiel the spare. "This is an all-expense paid trip Miss Milton so please don't worry about any costs of room service and the like. If you should require anything then please just ring down to reception and they should help you. There is an itinerary upstairs in your suite telling you when you shall be meeting Mr Winchester and of your plane times tomorrow evening. The hotel's concierge shall now take you upstairs to your suite and I hope you enjoy your evening." Chuck said. He gave Anna and polite smile then Castiel and more sympathetic smile that Castiel couldn't help but appreciate and a return. At least someone else out there knew how he felt at this moment in time. Once Chuck was gone Anna turned to her brother and gave his a look of pure awe and disbelief.

"I swear I am dreaming." Anna said with a slight giggle. Despite his reluctance to coming with Anna this weekend Castiel knew just how happy his sister was and seeing the look on her face made up for his own discomfort for just that brief moment. Giving Anna and genuine smile Castiel draped an arm around her shoulder and gave her a squeeze.

"Ready to charge some very overpriced food from the mini bar to one Mr Dean Winchester?" He asked with a slight smirk.

With a roll of her eyes Anna chuckled when she said "You, Castiel James Milton, are incorrigible."

* * *

**Author's Note: Once again thanks so much to everyone reading and reviewing this. I'm glad you're all liking it so far!**


	5. Chapter Five

**Chapter Five**

"Castiel" Anna said with a whine as she walked into the main sitting room of the hotel suite. She was holding at least four dresses and her hair was still wet from the shower she'd recently taken. "I need you to be a girl for five minutes" she begged. Castiel turned back to the documentary he was watching and pretended that he hadn't heard his sister. True they had actually had a good day in New York. They'd gone on the subway and taken touristy photos to send back to Gabriel in Central Park. Anna had wanted to visit the Alice in Wonderland statue by Conservatory Water because she had been obsessed with books when she was younger and Castiel had wanted to go to the William Shakespeare statue near Sheep Meadow. They had sent Gabriel the photos of the pair of them and Gabriel had swiftly replied with a text message telling them that they were both nerds and couldn't they find anything better to do in New York than take photos of statues? "Castiel…please be a girl for just five minutes." Anna said snapping her fingers to get Castiel's attention.

"There is nothing good in that sentence." Castiel muttered under his breath

"Please, Castiel! I really need your help. I don't know which dress to wear." Anna said holding up her dresses and looking frazzled.

"I hate to ask but why couldn't you have dragged Ruby here with you?" Castiel asked "She would have been a lot more helpful than me because all those dresses look exactly the same to me."

"They're all different colours." Anna said with irritation.

"They're all dresses; they really don't look any different. Now why couldn't Ruby come with you?" Castiel asked for what felt like the millionth time.

"She had a paper to write plus there was an 'amazing' party at some guy's house that she couldn't miss." Anna explained. "Now please help me." She added pleadingly.

"Do I really have to?"

"Yes, now tell me which dress to wear. Oh and will my hair will look better straight or curly?" Anna asked.

"I really have no idea Anna why can't you ask someone else?" Castiel asked

"I swear to God or Oprah, whoever is more powerful, that if you do not help me I will enlist the help of Gabriel and make you pay." Anna said with a low growl that was actually quite threatening.

"Ok, ok. Don't wear the red dress because it's too short and you'll look like a hooker. The blue dress is ugly and the purple dress will make you look like Aunt Rachel. Wear the black one. Just like your hair dry naturally because it looks nice now can I do back to being a guy now?"

"Yes, thank you Castiel." Anna said hurrying up and giving Castiel a quick hug before she went back into her room, dresses and all.

* * *

There were countless times that Dean had been made to wear and suit and, except for Sam's high school graduation, he'd felt like a complete tool every single time. Now he stood in front of the mirror in his bathroom and thought that he looked like a kid playing dress up.

"Dean will you hurry up? You're going to be late if you don't hurry up!" Pamela snapped from in the sitting room. Dean sighed to himself and dragged himself out of the bathroom to the main room where Jo, Sam and Pamela were all sat.

"Oh will you just look at you all dressed up and dapper." Jo said grinning as she put her feet up on the coffee table and cracked open a bottle of beer.

"Feet." Dean snapped glaring at Jo's boots. Jo sighed and lifted her feet off the coffee table dramatically.

"God, you are so freaking anal about this damn coffee table." Jo muttered loudly another generous swig of her beer.

"It's a nice coffee table! I'm allowed to have a nice coffee table ok?" Dean said in defence of his love for this coffee table. The damn thing came all the way from Scotland; he was allowed to be anal about it.

"You disrespected the coffee table Jo, you've hurt him deep." Sam said with a small smirk.

"Alright children, can we stop talking about a coffee table now?" Pamela asked with a roll of her eyes. "Ok Dean please remember the golden rules of the evening. No liquor, no smoking, no swearing and no fornicating." Pamela said sternly. Dean was tempted to roll his eyes but nodded in agreement instead because it was easier to do than to protest. "If you screw this evening up I will butcher you." Pamela warned glaring at Dean for a moment before her attention went back her phone as it buzzed. "Oh and wear the green tie because it looks good with your eyes and don't put too much gel on your hair or you'll look like a prepubescent fourteen year old virgin."

"Pamela has a point." Jo said from where she was sat next to Pamela. Dean chose to ignore Jo's comment.

"Yes, thanks for that Pamela. That was really helpful." Dean said derisively.

"Well that's why I'm here." Pamela said sweetly as she tapped away on her phone.

"Maybe you could be more helpful by getting me that role in _Division_." Dean muttered.

"I'm working on it sweetie." Pamela said. "They're still taking a breath though I am hearing some good news which is positive."

"Good because the last thing I need is to lose out on a role thanks to the likes of Aston freaking Kutcher." Dean said grabbing the green tie Pamela had suggested and quickly tied it around his neck.

"They're looking for credibility when it comes to this film; there is no way the role will go to Aston Kutcher." Pamela said finishing up typing then throwing her phone onto the seat next to her. "Right let me look at you" Pamela said looking up at Dean. "Is that the Hugo Boss or the Armani suit?"

"I have no idea Pamela, it's a suit." Dean said feeling very much like a children playing dress up again.

"Fine, it looks very good either way. Now tell me the golden rules." Pamela said looking Dean up and down.

"Pamela-"

"Dean, tell the woman the damn golden rules." Jo said with a huge smirk on her lips.

"Fine. No liquor, no smoking, no swearing and fornicating. Are you all happy now?" Dean asked looking at Jo, Pamela and Sam who were sat with various smirks on their faces. For that moment Dean hated them all for how much they were enjoying his misery.

"Very happy." Pamela said clapping her hands together. "You screw this up and I'll make you wish you were in hell because that would be more pleasant than the pain I will inflict upon you."

"You scare me sometimes Pamela" Dean admitted.

"Good. Now get going or you'll be late." Pamela said flapping her hands to make Dean leave the apartment. Dean looked back at Jo and Sam and saw their expressions; Jo's was merely a mocking smirk while Sam's look semi-pitying. Neither of these looks helped whatsoever. Great, just great.

* * *

Dean breathed in deeply and knocked on the hotel room door. This was the moment of truth and he really hoped that this Anna girl wasn't some crazed looking fan. For what was probably the millionth time he was wondering why he ever agreed to let Pamela arrange this.

The door opened and Dean was about to give this Anna girl his most winning smile until he realised that the person who had opened the door was certainly not Anna, unless Anna was a scowling guy with messy dark hair and bright electric looking blue eyes. Dean found himself unable to speak and he really wasn't sure why. This guy looked him up and down, with one eyebrow cocked, without blinking once and Dean found it really had to stop looking at the guy's face. What the fuck was wrong with him?

"So can you only speak when it's written down on a script for you?" The guy asked as he continued to stare at Dean with that stupid cocked eyebrow and a small smirk on his full looking lips. Ok then… "I could wait here while you get a scriptwriter if you want?" The guy then said still with that damn smirk. Oh yeah, Dean was still looking at this guy and he still hadn't said a word. It was probably the smirking scowl or the sarcasm that had gotten to Dean. At least that's what he hoped it was.

"Sorry I'm Dean, I'm here to pick up Anna." Dean heard himself stutter. Since when did he fucking stutter?

"Yes well that is kind of obvious." The guy said still smirking at dean with a condescending look upon his face. "Well you better come on inside. I'm sure you're not used to being made to stand in a doorway waiting on people so we wouldn't want to hurt that precious Hollywood ego of yours." The guy added moving away from the doorway and walking back into the hotel suite. Dean followed inside to the large suite that looked like several of the hotel suites Dean's had stayed in over time. The only difference was the huge pile of books on the sofa, well of which looked very well read. Dean noticed the very familiar cover of _Slaughter House Five_ and couldn't help but smile seeing as it was one of his favourite books. Dean suddenly noticed that the guy was looking at him smiling at the pile of books.

"Um…Vonnegut, it's a nice choice." Dean said nodding at the book. The guy's eyebrows shot up in surprise. He probably thought Dean had never read a book in his life.

"Yeah, I needed something riveting to read on the plane to distract me from Anna's excitement." The guy said with a casual shrug before he turned away from Dean quickly. "Anna!" He called out towards a door leading off from the sitting area. "Hollywood Ken is here for you and he's all suited and booted." He added looking back at Dean and giving him yet another smirk. Dean was tempted to give this guy a smirk of his own but he had been completely thrown by the 'Hollywood Ken' comment. Only his family and Jo, who he considered family, gave him any sort of grief about his career and now here was this random guy standing in front of him smirking and giving Dean thinly veiled shit. Dean was trying to think if some sort of comeback when a door opened and a pretty redhead walked into the room and smiled nervously at Dean. Her hair was loose and hanging down her shoulders in waves and her black dress clung to her body without looking in any way cheap. Dean's luck was looking up.

* * *

It was probably the weirdest yet most amusing situation Castiel had ever been in during his life. Dean Winchester seemed unable to say anything remotely coherent unless it was written down for him and hopefully Anna would see what an idiot the guy was and that would be the end of her infatuation with the guy. Maybe Castiel could go to the cinema from now on without having to sit through two hours of Dean bloody Winchester attempting to act. Ok maybe the guy was good looking but looks do not equal talent in Castiel's eyes.

Anna came into the room all nervous looking smiles and stopped when she saw Dean. Castiel was glad she didn't scream or squeal because that would have made his twenty-two year old twin seem about thirteen and slightly insane.

"Oh God, hi. It's really great to meet you. I'm Anna but you know that already I'm guessing." Anna gabbled and Castiel refrained from rolling his eyes for what would be the millionth time that day. Anna was normally an intelligent person who didn't gabble but when Dean Winchester was involved that kind of got shot to hell.

"It's a real pleasure to meet you Anna." Dean said walking up to her and giving her a kiss on the cheek. If it wasn't so cheesy Castiel might have thought it was slightly charming but at least Dean wasn't flat out hitting on his sister like he probably did with every other woman in the world.

"It's a pleasure to meet you as well." Anna said sounding quite gushing. This was pretty new for Castiel to see as his sister never gushed in front of anyone so seeing her acting like this was very strange for him to witness. Castiel thought he'd save his poor sister by faking a cough and Anna jolted a little like she had forgotten that Castiel was actually there. "Oh this is my brother Castiel." Anna said grinning at Castiel; he couldn't refrain from smiling at his sister because at least she looked happy tonight. Dean reached out to shake his hand which Castiel reluctantly accepted more because he'd been raised with manners than the fact that he wanted to shake Dean's hand.

"Good to meet you man." Dean said shaking Castiel's hand.

"I didn't catch the name, Dean was it?" Castiel said with a grin and he saw Anna roll her eyes with annoyance. At the sake of his sister's temper Castiel couldn't help but mock Dean Winchester. When would he get the chance again?

"Yeah." Dean said almost giving Castiel a smirk. Without saying another thing to Castiel, Dean turned back to Anna with a smile on his face. "Well we have reservations for eight so shall we get going?" He asked. Anna nodded happily then looked at Castiel.

"You're not going to be bored here by yourself?" Anna asked him. Castiel shook his head with a sarcastic snort.

"There's no chance of that, according to the guy in the lobby there is a great cinema just a short subway ride from here that shows some good independent films so I plan on seeing some good cinema for once. Also this is _New York_, I'm not sure it is possible to be bored in New York." Castiel said.

"Well you try to have fun and try not to overindulge on crap." Anna said

"Same to you Anna, same to you. You two have a good night." Castiel said smiling sweetly at both Anna and Dean before he went into his room to get a sweater. He heard Anna say something before the main door of the suite opened then shut leaving Castiel alone. Thank God for that.

* * *

As per Pamela's wishes Dean was a complete gentleman towards Anna the entire time they rode down in the elevator then towards the limousine that was waiting for them. As Anna beamed at him happily Dean could believe that this was a real date until he saw the flashbulbs of cameras outside. Yeah, he could pretend this was a regular date all he wanted but the press would certainly make him remember that everyone in America who read _People_, _OK!_ Or any other of those terrible magazines that loved to print photos and incorrect articles about him all the time.

"I'm really sorry about this." Dean said nodding towards the outside of the hotel where the paparazzi were waiting for them.

"It is really ok Dean; you must be used to it by now after all this time." Anna said looking towards the paparazzi nervously but then smiling up at Dean.

"You would think…but no." Dean said with a small and genuine smile. "Just keep your head up and smile…oh and try not to blink too much and don't stop to talk to them or you will never get away." Dean advised as he and Anna started to walk towards the hotel's main doors and paparazzi. The doors opened and the noise of cries and shouts from the paparazzi hit Dean like a wave. He should have gotten used to this seeing how the paparazzi had been hounding him for years but he really wasn't and it sometimes pissed him off how interested these people were by his life.

"Dean! Dean!" people cried from all angles. Dean just carried on looking ahead and smiling because that was the easiest thing to do.

"Miss Milton! Miss Milton! Who are you wearing?" someone else yelled loudly. Dean glanced at Anna and was thrilled to see that she didn't look too freaked out by the blinding flashbulbs. She was just smiling happily and looking straight ahead.

"Is that Milton with one 'L' or two?" someone else yelled. Anna seemed to have taken Dean's advice well and didn't stop to talk to the reporters. The pair of them carried walking towards the limousine with Dean opening the door for Anna when they reached the limousine. This seemed to send the reporters and photographers into overdrive as they clamoured for photos and quotes from Dean or Anna. Dean just gave them all a quick smile knowing that Pamela would be desperate for one really good photo taken of him or she would yell at him for a good fifteen minutes in the morning.

"Wow…well that was…very intense." Anna said with a nervous chuckle once they were inside the limousine. "Do the spots in front of your eyes go soon?" Anna then asked.

"Yeah don't worry, they should be gone in a few minutes…blinking rapidly doesn't help though." Dean said. "I learnt that from experience"

"I can't believe you have to put up with that all the time." Anna said sounding vaguely awestruck.

"Not all the time, I've invested in some hilarious disguises with my friend Jo over the past few years." Dean said laughing at the memory of the time he and Jo dressed up as Robert Plant and Patty Griffin so they could go out to a club opening. It had surprisingly worked and Dean hadn't been plagued by people at all that night. Then there was the time three years before when Dean, Jo and the very disgruntled Ellen and Bobby had all dressed up as stereotypical rednecks to take Sam to Disneyland. The photos, some of which hung up in Dean's bedroom, were some of his favourites just because of how ridiculous they all looked and how freaking happy Sam had looked.

"That sounds really fun actually. That seems like something I'd do with Castiel actually." Anna said giving Dean yet another smile. Thank god this girl seemed relatively normal and she wasn't one of those 'scream and cry' fans. "I could imagine that it nice to be able to go out and not have people realise who you are sometimes." Anna said. Dean really looked at this girl and thought that what she was saying couldn't have been more true. As she continued to smile at him Dean found that he was so relieved that Anna seemed normal and actually pretty cool.

* * *

"Reservation for two under the name Winchester." Dean said to the hostess once he and Anna entered the relatively busy restaurant. The hostess stopped for a moment and her eyes grew wide when she realised who Dean was.

"Of course Mr Winchester, please do follow me. We have reserved the best table for you Mr Winchester." The hostess said. "It's a pleasure to have you with us this evening an can I just say that I am a _huge_ fan" the hostess purred smiling in a way that might been because she was coming on to Dean…even though it was clear that he was on a date with Anna. Women confused Dean sometimes.

"Thank you." Dean said pleasantly as they walked through the restaurant. The hostess stopped at the nicest table in the restaurant and smiled yet again.

"Here we are, your waiter will be over soon to take your drinks order." She said.

"That's great, thank you" Dean said with a smile as he held the chair out for Anna. The hostess gave Dean another blatantly obvious smile before walking off but not before glancing behind to look back at Dean.

"Wow…" Anna said raising her eyebrows.

"What?" Dean asked.

"She was not subtle." Anna said as she began to laugh. "I bet you get that a lot though don't you?"

"It happens far too often actually, you wouldn't think it didn't get tiring but it actually does." Dean said with an embarrassed smile.

"Does it hurt? Smiling like that all the time?" Anna asked cocking her head to one side.

"Not really, after you've been doing it for so long it doesn't hurt that much. It gets you in the cheek area after a while though." Dean explained. "So, have you had fun in new York so far?"

"Oh yeah. I've never been outside of Illinois so being here is pretty amazing. Castiel and I went to Central park and took so many photos of the statues and the trees which sounds a lot more lame than it actually was." Anna said with a small chuckle.

"Don't worry it's not lame to geek out over Central Park. My brother Sam has this insane amount of love for the public library and when he comes here that's where he spends most of his time. New York is great for people who loves things other than football or stuff like that. So what else do you plan on doing while you're here?"

"Well I really want to go to The Met to see some of the exhibitions and I promised my brother I would go to Dylan's Candy Bar." Anna explained. "He's given me eighty dollars and said that if I don't spend all of that on candy then his disowning me." Anna added shaking her head.

"God my brother loves that place." Dean said shaking his head as he remembered the last time Sam had been inside the famous sweet shop. It had certainly been an experience.

"Mine too! He's been going on about it for weeks ever since he found out about me coming here" Anna said excitedly. Seeing her face light up when she talked about her family made Dean think about how Jo's face lit up when talking about Ellen or Bobby.

"Do you just have the one brother?" Dean asked. Hopefully Anna would answer with 'Yes' so there wouldn't be any more dark hair scowling guys with intense stares that clearly disliked Dean though when he thought about it the scowling guy did not seem like the Dylan's Candy Bar enthusiast. Maybe he hid it well.

"No, I have a younger brother called Gabriel. He's the Dylan's Candy Bar aficionado." Anna explained. Well there goes that hope.

"Wait, Gabriel? Like the angel?" Dean asked.

"Yeah, it's the biggest case of irony ever as well. He is anything _but_ angelic. If he manages to graduate from high school without killing, paralyzing or impregnating someone then Castiel and I will be so proud" Anna said raising her eyebrows with a snort. Dean found himself chuckling as that was what Bobby used to say about him when he was at high school before he dropped out to pursue his acting career. "It's funny just how rebellious Gabriel is really. He's a right little shit sometimes as well and he drives Castiel crazy most of the time." Anna added stabbing at her food.

"Are you close with your brothers?" Dean asked. Anna's face when she spoke about her family really did remind Dean of how he or Jo looked when they spoke about their respective families. It was clear that Anna was really close to her family and that was comforting to Dean seeing as he was close with his own brother.

"Yeah, well I live with Castiel as we go to the same university. I'm closer to Castiel than I am to Gabriel but I think that's because Castiel and I are twins." Anna explained.

"So you're a student?" Dean asked realising that he didn't know what Anna did.

"Yeah, at the University of Chicago. I'm in my final year." Anna said sounding proud of herself.

"How's that?" Dean asked. Part of him thought he might have missed out on the whole 'going to college' experience seeing as he'd dropped out of high school for his acting career so he was actually really interested in hearing about Anna's college life, he wasn't just doing it to be polite.

"It's pretty damn cold most of the time and so I end up drinking my weight in coffee most days." Anna said with a chuckle which Dean joined in with. "I really love it though. I have some good friends and obviously I get to spend so much time with my brother. My course is truly fascinating as well."

"What are you studying?"

"I'm studying History of Art. It is an incredible subject to study apparently I've designed myself for a life of slacker jobs according to the less than supportive members of my family." Anna said raising her eyebrows with a smile.

"Well I had people telling me that I wanted to become an actor if it's any consolation. My family and friends all pretty much laughed at me when I told them I wanted to move to New York and pursue acting." Dean said.

"And yet here you are." Anna said with yet another impossibly bright smile.

"And yet here I am." Dean said.

"If it's any consolation to you I think you made the right choice. I mean you've made millions of people happy with your films and the characters you have portrayed. No one can blame you for wanting to be a part of an art form that inspires so many people, emotes with them and moves them on personal levels can they? True many people might think that wanting to act is soft or silly and vapid but it's not really. You're telling us a story, a story that can transport us to somewhere entirely different for a few hours but then we remember the characters, we absorb their story and we remember them even after the credits have rolled by. Yes some of your friends and family might have laughed at you and said that you had designed yourself to a life of disappointment and idle jobs but really your threw yourself into a world of endless possibilities." Anna said seriously and Dean found himself unable to look away from her absorbing gaze. Her words resonated so deeply that there was no possible way of looking away from her; she spoke words of comfort without sounding pandering or remotely patronising. She simply told Dean what she thought was the truth and it was words that Dean didn't realise he needed to hear until that moment.

* * *

Castiel was walking towards the nearest subway station in his quest to find the cinema. He'd never been to New York, heck he'd never been out of Illinois before so he was enjoying being in a city full of culture. He and Anna had a full day in New York tomorrow and Castiel was already trying to think of things they could do. He wanted to go to the Strand and scour the eighteen miles of bookshelves if he could convince Anna. They might have to stop at The Metropolitan Museum of Modern Art because Anna would get a kick from the exhibitions as Anna loved art.

Castiel was about to enter to the entrance to the subway when his phone buzzed. He looked at the screen and frowned when he saw Ruby's name. He constantly forgot that Ruby had his number and vice versa. Castiel only had it in case of emergency so Ruby texting him now was a bit out of the blue. He opened the message then rolled his eyes once he read it.

**Ruby:** _Has Mr Fine Ass turned up to sweep Anna off her feet yet? _

**Castiel:** _I wouldn't know about his ass seeing as it was covered by a suit but the glitter covered eagle has left the building._

**Ruby:** _Dean Winchester in a suit. If Anna can keep her hands to herself then she is a fucking nun._

**Castiel:** _Please don't talk about my sister groping Dean Winchester; I don't want to be mentally scarred for life thank you very much._

**Ruby:** _Hey I never said anything about groping. I was thinking more horizontal and less clothed._

**Castiel:**_ I'm not texting you anymore if you're going to say mentally scarring things like that._

**Ruby:** _Sorry Cassie ;)_

Castiel refrained to texting Ruby back in protest of her calling him Cassie but he knew there was no point; Ruby would carry on calling him that just because she knew it drove him round the bend.

**Ruby: **_Ooo can you ask Anna that if she gets married to Mr Fine Ass then can I be maid of honour?_

**Castiel: **_Wouldn't that require you to have some honour in the first place?_

**Ruby: **_Touché Milton, touché. _

Castiel was about to pocket his phone and grab the subway to the cinema but the phone burst to life with a shrill ring. Glancing at the I.D on the screen Castiel braced himself for a moment before he answered the phone.

"Hello Gabriel" He said hoping that the first sentence out of his brother's mouth was not going to be about Dean Winchester.

"So…is she on the date?" Was the first thing Gabriel said without even saying hello. So much for Castiel's hope.

"Is that the only reason that you're ringing me?" Castiel asked

"No, of course not. I have other reasons to be calling my big brother!" Gabriel said cheerfully.

"We haven't gone to Dylan's Candy Bar yet but we have your eighty dollars and your list that includes something called the Gum-believable Mix and the Clodhoppin' Good Time Mix." Castiel said shaking his head at his brother. The list had been incredibly long and had included strict instructions to not forget a single item or the list or Castiel and Anna would experience 'The Wrath of Gabriel Milton'…whatever that was.

"You _dare_ forget my Gum-believable Mix and I will disown both you and Anna, I swear to Oprah!" Gabriel cried so loudly that Castiel had to move his phone away from his ear.

"Anna and I are not going to forget your Gum-believable Mix. You wrote it down in capital letters, underlined it four times _and_ highlighted it." Castiel said with a roll of his eyes.

"Good!" Gabriel said cheerfully sounding like a four year old "Now tell me all about Hollywood Ken." He added suddenly sounding like a lecherous teenager. How did he manage to switch so quickly?

"Why can't you just ask Anna tomorrow then both of you can bask in Dean Winchester glory?" Castiel asked.

"Because it's so fun hearing you be all snarly and snarky over Mr Dean Winchester" Gabriel said chuckling. Castiel could just imagine the little so and so sitting in his room and smirking away knowing that he was going to be getting overpriced confectionary and gossip about Dean Winchester.

"Gabriel I'm not going to help with whatever weird fantasy you are going to get about Dean Winchester from Anna's evening out with him." Castiel said as he neared the cinema. "Now are you only ringing to question me about confectionary and Dean Winchester?"

"Pretty much so." Gabriel said cheerfully. Castiel couldn't help but roll his eyes. Was it so much to have one person in his life not obsessed with Dean Winchester?

"Well that makes me feel very much loved by my brother." Castiel said, his voice dripping with sarcasm which he knew would no doubt annoy Gabriel but he couldn't help it. "I'm about to go and watch a film so is there nothing else you want to talk to me about?" Castiel asked.

"Oh God, you go and enjoy whatever depressing indie film you're no doubt going to see. I'll ring Anna in the morning, there is only so much of your snarl I can deal with at one time dear big brother" Gabriel said. Castiel swiftly said his goodbye to his brother and hung up the phone. The next few hours would be bliss, sitting in a New York cinema experiencing a decent film, and there was no way that Castiel was going to pass it up even if his brother no doubt found him boring.

* * *

Dean was genuinely amazed by how well he was getting on with Anna. Her anecdotes about her life in Chicago with her brother and her best friend, a girl called Ruby as far as Dean could remember, were actually pretty interesting. Anna was pretty and seemed quite smart. After about half an hour Dean really had forgotten that Anna was the 'Win A Date' girl and Dean just kept seeing her as a normal girl he was out on a date with. He was actually disappointed when the date came to an end and they were riding in the limousine back to Anna's hotel.

"It was a pleasure meeting you tonight Anna." Dean said smiling at Anna as he watched her smile in awe over the New York nightlife they were passing.

"I was a lot less crazy than you were exacting wasn't I?" Anna said turning back towards Dean giving him a knowing smirk.

"See now that you've said that I feel like less of an asshole for thinking it." Dean admitted.

"So does that make me more or less of an asshole for saying it?" Anna asked raising an eyebrow.

"Oh definitely less, definitely less." Dean said giving Anna a truly genuine smile because she was actually really funny and pretty damn awesome.

"Well that's very good to know. You were very much the gentleman as well." Anna said. The limousine came to a stop outside the hotel and once again it was crowded with photographers. Dean gave Anna an apologetic look before he opened the door and helped Anna out. The flashbulbs went off like fireworks and the shouting started up again. Taking Dean's advice from earlier on Anna just carried on smiling and walking along with Dean into the hotel. They rode up to the penthouse in comfortable silence. Once the elevator stopped Anna gave a small chuckle.

"Well, this is me. That's probably the last time in my life I can say that about a penthouse suite but oh well." Anna said. Dean couldn't help but chuckle along with her. Taking Anna's hand Dean gave her quick and sincere smile.

"Goodnight Anna." Dean said giving Anna a quick kiss on the cheek. She beamed up at him and Dean saw a slight blush creep along her cheeks.

"Goodnight Dean, thank you for a truly wonderful evening" Anna said happily as she opened the door to the penthouse. "It really was a pleasure meeting you, thank you." She added. Dean gave her another smile before calling the elevator. Anna gave him one last beaming smile before shutting the door. Dean was still smiling and looking at the penthouse suite door when the elevator doors opened. If he had been looking at the elevator doors he would have known that someone was inside and he wouldn't have bashed into them.

"Shit, I'm sorry." Dean said quickly looking down slightly at the shock of messy dark hair. With a loud huff the person he'd bashed into lifted up their head and looked at Dean. Dean's heart sunk when he saw that it was Anna's brother, Castiel, and he didn't look too impressed that he'd nearly been sent flying by Dean.

"It's fine, I guess it's hard to see the little people from up there in 'Movie Star World'" Castiel muttered. "Well at least I know Anna's made it back safely and wasn't eaten alive by paparazzi." He added but this could have been more to himself than towards Dean.

"Um…" Dean heard himself mumble because he was actually terrified of saying something that would piss this guy off even more.

"Save it, we don't want to scrambling that pretty head of yours looking for a coherent sentence to stutter out." Castiel said with a roll of his bright blue eyes as he walked towards the penthouse doors and pulled a key out of his back pocket. Not that Dean was looking at his back pocket…

"Did you like the film?" Dean heard himself stutter out and once again he was cursing himself because he was Dean Winchester, Dean Winchester did not stutter. Castiel looked back at him with a surprised look that still seemed to be mocking Dean.

"Yeah I did actually. I didn't have to pretend to have stayed awake for the whole thing, unlike most movies I've seen in cinemas." He said. "Well goodbye Hollywood Ken and I hope you were everything my sister hoped you would be." Castiel said giving Dean a derisive salute before he went inside to the penthouse leaving Dean standing there, having to call the lift again, and, Dean really had to admit this, vaguely confused.

* * *

**Author's Note: So they've met, yay. I love writing snarky Cas. Hopefully you liked the chapter!**


	6. Chapter Six

**Chapter Six**

Anna was lying face down on the couch when Castiel left Dean Winchester standing in the hallway. Anna's position was either because the evening had been terrible so she was now in mourning of her appreciation of Dean Winchester or the evening had been so wonderful that Anna was now lying down because if she didn't then she might freak out. Castiel wasn't sure which one he wanted to be more real.

"Anna?" Castiel asked. Anna gave him no reply. "Anna…Anna, was tonight's excursion with Dean Winchester everything you hoped it to be and more?" Castiel asked walking up towards his sister. Anna rolled over onto her back and the smile on her face was so large and beaming that Castiel's answer was swiftly answered without Anna having to say a word. "It was _that_ good then was it?" Castiel asked unable to stop smiling seeing the joy on Anna's face.

"Castiel…it was amazing. Dean was so genuine and funny. We talked about so much and he's a really decent guy." Anna said dreamily before she frowned slightly. "You're going to get bored by this aren't you?" she asked.

"No, you obviously want to talk about it so tell me about the evening." Castiel said with a shrug of his shoulders.

"Are you sure?" Anna asked sounding sceptical.

"I'm not an asshole Anna; I'm actually interested in hearing about your evening before it's oversaturated by the mass media of America." Castiel said. "Now shift over so you can tell me about your 'delightful' evening with Mr Winchester." Castiel added while Anna up so Castiel could sit down next to her.

"It was…it was so amazing Castiel. It really was. He's so different from what I thought he'd be like in a good way. I was kind of worried that we would have nothing to talk about whatsoever and yet the conversation never stopped, it never felt forced or anything like that. We talked about I did at college, my artwork and my family. He was so interested in it and it never seemed like fake interest at all. I mean he's _Dean Winchester_ so he could easily pretend that he was interested in what I was saying and not really mean but he wasn't. He was so genuine and funny. It was just a really perfect night and I cannot believe that it actually happened." Anna said dreamily as she smiled with a blissed out look on her face. Seeing Anna this happy was one of the greatest things for Castiel to witness. Anna had gone through a bad breakup during their second year of university and it had cut her very deep. Castiel remembered nights of having to sit with Anna in her room as she sobbed herself to sleep over her ex-boyfriend. It had taken nearly three months before she would even start going out for nights out with Ruby and even then Anna was wary around guys. Seeing her this happy after a night out really made Castiel happy even though it was obvious that Anna would never meet Dean Winchester again. At least she was happy and that was what mattered to Dean.

"So Hollywood Ken was a complete gentleman then?"

"Yes Castiel, Dean Winchester truly a gentleman." Anna said giving Castiel a nudge with her elbow. "I'm very surprised by the radio silence from Ruby. She refrained from sending a smutty text message all evening, I'm very proud of her. I was expecting a healthy slew of them."

"That may be because she decided to bless me with her inappropriate opinions instead." Castiel with a roll of his eyes.

"Well now I feel truly sorry for you for having to put up with that."

"Oh you should, Ruby is still insisting upon calling me 'Cassie' at every opportunity that she gets." Castiel said while Anna hooted loudly with laughter. Castiel nudged her in the side. "Oh thank you for your support. I'm going to bed and not listening to you go on and on about your evening with the talentless moron Winchester now." Castiel said pulling himself up from the couch.

"Oh Castiel, I'm sorry I laughed ok? Now sit back down so I can bore you stupid with every single detail about my evening." Anna said pulling Castiel back down onto the couch.

"Do you really have to?" Castiel asked because even though he loved Anna he wasn't sure how much he could hear about Dean Winchester without wanting to shove pencils into his ears

"Yes." Anna said firmly. Well that was the end of that discussion clearly.

"Fine but if you're still telling me Dean Winchester related shit at three in the morning then I'm disowning you and demanding that you let me sleep otherwise we won't be able to do anything tomorrow before we're due back on the plane for Chicago. Deal?" Castiel said settling himself in the seat because he knew once Anna started talking she wouldn't stop.

"Deal." Anna said smiling brightly as she launched into her story and Castiel instantly regretted being such a good brother.

* * *

The journey back to his apartment from the hotel was not long yet it still gave Dean a chance to think. Maybe Pamela had done something right with this evening. Yes it had been the pain in Dean's ass for several weeks but Anna had been so different from what he had been expecting; she had been funny yet intense with a way of saying things that actually resonated with Dean, things that actually made him think. Anna had been a total surprise in every way, in every good way actually even if her brother seemed to be a sarcastic and conceited dick. Even so he was a sarcastic dick with quick wit and an interestingly attractive smirk, though Dean was determined not to think about that as it would just cause Pamela to yell at him again. He tried to keep Pamela's yelling to a bare minimum, three hours a week maximum.

Jo and Sam were sat, both with their feet up on Dean's damn coffee table, on the couch drinking beer and watching a National Geographic documentary about God only knows what when Dean finally got back to his apartment. To be truthful he wasn't remotely surprised by how at home both of them looked. After all, Jo practically lived in Dean's apartment most of the time and when Sam wasn't in Palo Alto he was in New York staying with Dean as returning home to Kansas, seeing their old family home, wasn't something either brother sometimes wanted to do. Plus Sam always got a kick out of spending half of his life in New York's endless bookstores and libraries.

"Well hey there Romeo" Jo called out when she saw Dean. Sam gave Dean a smirking grin that Dean quickly returned. "How did the ol' date go? Was she an ugly crazed hillbilly?" Jo asked raising her bottle beer as a salute.

"She was from Chicago so she wasn't a hillbilly." Dean pointed out. "And for the last time get your damn feet off my fucking coffee table. Move your damn legs Sasquatch." Dean added walking up to Sam and whacking him on the leg.

"Ow, jerk." Sam muttered under his breath glaring up at Dean with a scowl.

"So…she was crazed and ugly" Jo said grinning while she removed her feet from the coffee table.

"Actually she was pretty damn awesome and hot so, at the risk of sounding like a child, _there_." Dean said sneering. Jo raised her eyebrows in surprise and let out a small laugh.

"As if. She at least had to be crazy." Jo said.

"No, she was perfectly sane and seemed to have a good time."

"If she thought a night out with you was a 'good time' then she must be freaking crazy." Sam said earning a high five from Jo.

"I'd like to point out that both of you are sat on _my_ couch, drinking _my_ beer and watching _my _television. If you carry on with this bullshit then I could just kick you both out."

"If you do then I'm selling those photos of you from last Halloween to the papers. I'm sure they would love to print photos of you dressed up as Stevie Knicks." Jo said with evil smile across her face.

"_Why _have I _never_ seen these photos before?" Sam asked sounding mortally offended and hurt.

"Oh you wait; I even have a hilarious video of him doing a beautiful rendition of Dreams while using a bottle of tequila as a microphone."

"I really worry about you sometimes Dean." Sam muttered as he returned to drinking his beer and trying to watch the documentary that he and Jo had been engrossed in when Dean returned home. "Now are you going to sit down and be quiet so I can watch this or are you just going to stand there?" Sam asked. Dean took that as a cue to grab a bottle of beer that had been sitting on the coffee (with no coaster Dean wanted to point out but Jo would have given him grief no doubt if he said anything) and plonk himself down onto the couch next to Jo. The three of them carried on watching the documentary for at least an hour until Dean became bored as well as tired. The evening had actually been damn tiring and now all he wanted to do was crawl into his own bed.

"You staying here tonight?" he asked Jo after he announced he was going to bed.

"Go on then, I can't be bothered to drag myself to the subway to be honest."

"You never can. Don't stay up too long watching shitty documentaries." Dean said ruffling Sam's hair and giving Jo a friendly nudge.

"If I don't wake up to E! News speculating a wedding between you and the 'Win A Date' girl then I'll be very disappointed Winchester!" Jo cried as Dean walked to his room and practically dropped onto his bed. He could barely keep his eyes open as he removed his suit and changed into a worn t-shirt and old grey sweatpants. He crawled into his bed and let his head hit the pillow without any grace what so ever. Yes the evening had been tiring but Dean had to admit that it had been enjoyable, Anna's company had been enjoyable and Dean found himself smiling as he remembered the way Anna's hair hung down her shoulders and the bright smile across her face.

_"If it's any consolation to you I think you made the right choice. I mean you've made millions of people happy with your films and the characters you have portrayed. No one can blame you for wanting to be a part of an art form that inspires so many people, emotes with them and moves them on personal levels can they? True many people might think that wanting to act is soft or silly and vapid but it's not really. You're telling us a story, a story that can transport us to somewhere entirely different for a few hours but then we remember the characters, we absorb their story and we remember them even after the credits have rolled by. Yes some of your friends and family might have laughed at you and said that you had designed yourself to a life of disappointment and idle jobs but really your threw yourself into a world of endless possibilities."_ Dean heard Anna's voice say as he slowly began to drop off to sleep. Dean smiled yet again as he pictured Anna saying these words yet as he did so Anna slowly morphed into a smirking face with full lips, dark hair and bright eyes full of scathing looks. Shit…

* * *

Morning came too quickly and before Dean realised it he was being awoken by someone shaking and smacking his arm. Sam knew better than to try and wake Dean up in the mornings so this could only be Jo who really didn't care what mood Dean woke in as long he was awake so she could annoy him.

"Go away Jo." Dean grumbled.

"Nope, Sam got up early and jogged to that good bakery downtown. You know the one that makes those damn good pastries?"

"Jo I want to sleep, leave me alone." Dean groaned.

"He also got a stack of papers because your face is splashed across them."

"Fuck…"

"Yeah, exactly so get your ass out of bed. We want to witness your misery."

"I hate you so much."

"No you don't." Jo said was she strutted out of Dean's room.

"Yes I do!" Dean yelled as he groaned while dragging himself out of bed. Even though he could have done with an extra hour in bed he had to admit that the thought of fresh baked goods was too good to pass up.

"Yo Winchester! You're on Page Six!" Jo called from the kitchen and Dean couldn't help but let out another groan. The amount of times his name had appeared on Page Six was ridiculous and yet most of the time he never actually did anything to warrant being featured on the page. "It's not a bad photo actually; you're not squinting for once!" Jo added.

"That's great Jo." Dean called back sarcastically.

"And there's an article!" Jo said sounding far happier than she should at Dean's misery.

"Lovely." Dean muttered derisively. This would no doubt be the first of many articles on the date with Anna that Jo would devour so he should at least get it out of the way by reading this one…in private and away from Jo's, and no doubt Sam's, mocking. Dean padded out of his room and through the apartment until he got to the kitchen where Sam and Jo were sitting at the table drinking coffee and gorging themselves on fresh pastries. There was indeed a stack of papers on the table and Dean could see his face splashed across the front page of the first. Oh joy.

"You know she's pretty hot, not bad Winchester." Jo said looking at a photo of Dean and Anna leaving the hotel that was on Page Six. The smile of Anna's face was huge and Dean didn't look too surly for once. It actually wasn't that bad of a photo. "At least you're not doing that stupid face you always pull when you know someone is taking a photo of you." Jo said

"Hey, the Blue Steel is a classic look." Dean said grabbing a pastry.

"It makes you look constipated." Jo said with a grimace.

"You always look constipated." Dean shot back.

"Wow, you two are so mature." Sam said shaking his head. "It's bad when _I_ feel like the mature brother." Sam then said shooting Dean a disapproving look.

"Haven't you _always_ felt like the mature one though?" Jo asked.

"Well there was that one time when I was seven that I thought Dean was pretty mature." Sam said thoughtfully.

"And how long did that last?"

"About fifteen minutes." Sam said with a shrug earning a whack across the head from Dean. "Ow…_jerk_." Sam muttered rubbing the side of his head where Dean hit it. "Just for that I'm going to read the article out loud."

"You wouldn't"

"Oh I would" Sam said smugly grinning at Dean then making a grab for the paper. Dean made a grab for it at the same but Sam was too quick and gave Dean a satisfied looking smirk as he ruffled the paper.

"I'll stop paying for Stanford if you read even one word of that article." Dean said threatening.

"Yeah right." Sam said clearing his throat loudly while Jo settled herself into a comfortable looking position in her seat. _"Will The 'Win A Date' Girl Win Winchester's Heart?"_

"It does _not_ say that." Dean said.

"Oh it does." Jo said gleefully. "It is top notch journalism I must say."

_"Last night saw the date the world has been waiting for-"_

"Are you fucking serious? 'The date the world has been waiting for' who wrote this piece of shit anyway?" Dean asked groaning loudly.

"Some hilarious genius called Becky Rosen now carry on reading because this going to be fucking hysterical" Jo said clapping her hands happily at Sam. Sam coughed loudly then carried on reading with a smirk on his face. Dean very tempted to throw something at his brother's head and it would most likely be very heavy.

"You carry on reading and I will actually hit you with a picture frame." Dean said threateningly towards Sam who just smirked at him. "I hate you so much, you bitch." Dean muttered.

"Shut it Winchester and let poor Sam read the damn article." Jo said kicking Dean's leg from under the table.

"_Last night saw the date that world has been waiting for. Since the 'Win A Date With Dean Winchester" charity competition was announced people all across America were desperate to enter in the hopes of winning a date with America's favourite movie star. That lucky winner turned out to be Anna Milton, a student at the University of Chicago, from Lincoln, Illinois. The lucky winner dined with Dean Winchester at one of New York's most upscale restaurants, pictured below._

_"The pair seemed very close" said one source. "They were laughing and joking together all evening, you could certainly see the chemistry between the pair of them. You could certainly tell that they found one another attractive."_

"Who the hell is the source?" Dean asked.

"Probably some random waitress from the restaurant." Jo said with a shrug.

"I hate people" Dean muttered in a low grumble.

"I'm sure your fans will be overjoyed to hear that Winchester." Jo said.

"Excuse me; I am trying to read here." Sam said with a sigh.

"Sorry Sam-o, carry on" Jo said gleefully. Dean wanted to die.

"_The Win A Date With Dean Winchester competition has so far risen over $25,000 dollars for charity and now people all over the globe are speculating if a romance could blossom between Milton and Winchester._

_Turn to page seven for an interview with our body language expert analyse the couple on their night out._"

"How is this even my life?" Dean asked resting his head in his arms.

"This is what you get for being a slut." Jo muttered sounding smug. Dean looked up at Jo to glare at her and swiftly gave her a good kick on her leg because Sam had no idea what Dean done to piss off Pamela in the first place. Sam looked between Jo and Dean with a confused and questioning look. "_Anyway_…" Jo said making it obvious that she was changing the subject. Subtly was not one of Jo's strong points. "What are we going to do today?"

"Well _you're_ going to work. Your shift starts in two hours." Dean said smirking.

"Fuck." Jo groaned resting her head in her arms. "I hate Sundays." She mumbled.

"Sucks to be you" dean said smirking at Jo's misery because she hadn't done anything else but smirk at his misery since he woke up. "So while you're stuck hating your job I'm no doubt going to be dragged around every bookstore in New York."

"Can we go to Dy-"

"_Yes_ Sam, we can go to Dylan's Candy Bar so you can be a five year old girl high on E-numbers." Dean said with a sigh.

"Now I _really _don't want to go to work now that there's a possibility of getting candy!" Jo said whinged loudly. "I _hate_ being employed."

"Don't we all."

"There's a difference between your employment and mine Winchester. You get paid millions to pout at a camera. I get paid to serve over priced coffee to hipsters until the afternoon then overpriced beer to drunk hipsters in the evenings." Jo pointed out.

"I _don't _pout." Dean said.

"You _do _pout." Jo retorted.

"Go to work Jo." Dean quickly shot back and Jo quickly gave him the finger. 

* * *

"Calling all first class passengers for flight 786, New York to Chicago." A clear and loud voice called over the intercom. Castiel took his last swig of coffee then threw the paper cup in the bin as he rose from his seat. They had been sat in the large Starbucks at the airport for around an hour waiting for their plane back to Chicago. Castiel had been thankful for the time they got to sit down actually because they had been walking round New York all day. Castiel had to admit that he was exhausted and couldn't wait to go to sleep on the plane.

"Well that's us." Anna said happily picking up her carry on bag. "You know, I could get used to flying everywhere in first class" Anna to Castiel as they hurried towards the gate.

"Oh I see how it is, one weekend in New York and you're already used to the high life. Let me guess, it's the free alcohol isn't it Anna Milton?" Castiel said shooting a smirk towards Anna.

"I'd say that it is more to do with the extra foot room and choice of your own film actually." Anna said grinning happily at Castiel.

"I'm just happy with the free alcohol at the end of the day." Castiel admitted because the only thing better than alcohol was free alcohol you could drink while reclining in a very comfortable seat with a built in back massager. A built in _back massager_. Ok Anna did have a point, they could easily get used to first class flying.

"Well there's big surprise there Castiel." Anna said with a shake of her head.

The pair of them had enjoyed their final day in New York with Castiel successfully convincing Anna that they needed to take a trip to the Strand bookstore. Castiel would be living on Ramen noodles for the next month thanks to spending far too much money on books and even Anna had been overjoyed when she found an autobiography of her favourite artist. After a trip to The Met, and seventeen text message and three voice mail messages from Gabriel, they had indeed gone to Dylan's Candy Bar and spent all of Gabriel's money on overpriced confectionary full of sugar and E numbers. Both Anna and Castiel agreed to never be in the same room as Gabriel once he dived into the pile of sweets they had gotten for him as they would most likely kill him within five minutes.

"Thanks again for coming with me Castiel; it's really meant a lot to me that you've come with me even though you didn't want to come here." Anna said looping her arm through Castiel's as they dragged their bags along with them. Castiel's own duffel was at least twice as heavy as it had been when he got here thanks to the several books he had purchased for the Strand.

"It's fine Anna. I've actually had a really good time here." Castiel said smiling down at his sister because even though he really didn't want to go to New York with Anna because of Dean freaking Winchester, Castiel had to admit that the weekend had been fun. Their trips to Central Park, The Met and the Strand had been a lot of fun and Castiel couldn't remember the last time he'd had that much fun with Anna. "I'm glad that Mr Movie Star turned out to be everything you hoped he would be."

"Yeah. Me too Castiel. Me too." Anna said smiling to herself.

* * *

Castiel liked being invisible. He could go through the day without having people stare at him over anything and he really enjoyed that. True he had friends, people that he liked to spend time with but he enjoyed being able to walk through the campus and not have people stop him and say hello to him all the time. Sadly that seemed to have gone to hell since he and Anna had returned to Chicago the day before. All day people had been pointing Castiel out and he'd heard countless people muttering his name. Thank God he'd had a full day of classes to distract him from people whispering things all day.

He cycled the long way back home so he could think over the essay he needed to write and the book he was hoping to finish later that night. Once he got back to the apartment building he chained up his bike and walked into the lobby to check his mail box for the package he was expecting from . Yes his splurge at the Strand had cleared him out but the week before he'd brought several books from and he was still waiting for them to arrive. Anna was right when she said that Castiel had a book addiction. He wasn't even sorry at all though.

"Oh Castiel!" A girl called as soon as Castiel entered the apartment building. Castiel looked round wildly and saw Rebecca, a girl that lived down the half from Anna and Castiel. She was a nice enough girl and always said hello to either Castiel or Anna when she saw them. Now she was looking frazzled and upset which was something new.

"Oh hello Rebecca, what's the matter?" Castiel asked walking up to Rebecca as he continued to look worried. "Is everything ok Rebecca?" he then asked.

"Oh, it's just that I heard some loud noises coming from your apartment, almost like crashing noises. I'm not sure if Anna is in or not and I was about I ring her but then you came back." Rebecca said.

"She should be back from her class by now, I best go and check what's going on. Thanks for telling me Rebecca."

"It's fine Castiel. I hope Anna is ok, I saw her photos in the paper and she looked really pretty. Say hello to her for me please."

"I will Rebecca." Castiel said waving Rebecca goodbye and racing up the stairs towards his apartment. Rebecca was right; you could hear loud crashing and ranting coming from inside the apartment that sounded like someone was either attempting murder or the demolition of the apartment. Castiel swiftly unlocked the door and took in the scene of the apartment before he heard a massive shattering noise. Castiel ducked just in time to watch as Anna threw a plate at the wall and watched it shatter into pieces scaring the shit out of Castiel. Her face was full of such rage and sorrow; Castiel hadn't seen her like this in a long time and it was truly frightening. She swore loudly and bitterly, her words polluting the air with her anger.

"What the hell is wrong?" Castiel asked racing over towards Anna before she threw another plate. "Rebecca from next door said that she heard noises and it scared the shit out of her. What's happened?

"That bastard! That fucking bastard!" Anna screamed pointing at the answer machine. The small red light was blinking away with the knowledge of a message.

"Who?" Castiel asked. For one wild moment his mind drifted to Dean Winchester but how could he leave a message for Anna?

"Just listen to the damn message!" Anna screamed marching over to the machine and pounding the play button.

"Hey there angel" the voice of Anna's ex-boyfriend Ryan said filling up the room. "I saw you with that goofball Winchester you always liked in the papers and all over those shitty magazines you love. You looked amazing angel, so gorgeous. Listen I'm back in Illinois for a week or so, you should ring me angel. Say hello to that brother of yours and tell him there no hard feelings over that broken nose. Catch you later angel" then the message cut off. Anna stood, her breathe ragged and heaving.

Castiel felt sickened that Ryan would even think to ring Anna after everything he had done to her when they broke up. The temptation to break Ryan's nose again was coursing through Castiel's body. Instead he just walked back towards the kitchen and grabbed a stack of plates, he handed half to Anna but kept the other half for himself.

"Fifty points if you hit the pizza stain from the last time Gabriel was here." He said and Anna sighed loudly.

"Thank you." She said with a voice full of relief. "Really, what would I do without you?" Anna asked taking aim and launching a plate at the wall. It hit the pizza stain that Gabriel had called when he thought playing pizza Frisbee drunk with Ruby was a genius idea. "And that's fifty points to me!" Anna said happily wiping away a stray tear.

"That calls for pizza and a movie." Castiel said as his heart swelled seeing Anna smile. He would delete the message as soon as he could and ring Ryan to tell him not to ring Anna again. She was happy without him, she was better without him.

Castiel ordered a pizza for them to share and he even let Anna pick the DVD. While they waited for the pizza to be delivered Castiel and Anna sat down on the couch with cups of coffee. While Anna had been cleaning her face of tears Castiel had deleted Ryan's message so Anna wasn't tempted to listen to it again.

"Thank you for this, hearing his voice just made me so damn angry and I just couldn't think straight. It just after everything he did to me and everything he said to me when we broke up…why would he think to even ring me let alone say that I should ring him." Anna said.

"Anna it's ok, as long as you're not tempted to ring him."

"There's no way I'll ring him Castiel, don't worry. I would rather kill him than ring him." Anna said firmly.

"Well that's good to hear. I don't have to make it clear how much I hate that complete idiot. Now how did your first day back go after your face was splashed all over America's mass media?"

"Hectic...I woke up this morning to four hundred emails. I never get fourteen in a day let alone four _hundred_. Then Ruby and I kept getting held up all day by random people coming up to me and asking me countless questions. I was ten minutes late for my morning lecture on Renaissance art this morning because a group of girls cornered us when we were getting coffee." Anna said sounding tired. "Ruby came up with some convincing lie when we finally got to our lecture but it was still embarrassing walking in. Everyone turned to look at me and that stupid tool of a professor just smirked and made some shitty comment that I was too much of a celebrity to turn up on time." Castiel knew that Anna hated one of her professors with a burning passion because he never failed to undermine Anna at every opportunity.

"You really shouldn't let him get to you; you know what he's like." Castiel said. Anna had several choice words she liked to use when describing her main lecture, a pompous and rude middle aged man that went by the name of Zachariah Peters. Castiel had been forced to listen to far too many of Anna's rants about the man in the past.

"Yes but so many people were just staring at Ruby and I…it made me feel like I was under a microscope. I mean I don't regret winning the competition because the weekend in New York was amazing but now people are treating me so differently, people are actually noticing me now and it's a bit strange."

"But people aren't giving you hassle and grief are you?" Castiel asked worrying how down Anna now looked. Clearly pizza and a trashy film were needed.

"No not really but I can handle it either way. Though if I have one more person ask me if Dean kissed me then I will go insane!" Anna said. "Some random freshman even asked me to sign that picture of me in The Chicago Post. Ruby nearly wet herself laughing." Anna added. "I guess I'll just have to get used to people knowing who I am…even if it is only because I won some competition."

"At least it's not for the same reason that people know who Ruby is."

"Well she always does say that infamy is the best kind of fame." Anna pointed out.

"Yes well, she _would_ say that." Castiel said with a small snicker as the buzzer for downstairs rang. "I'll go and grab the pizza. You can pick but film but please choose something with a relatively decent plot."

"I cannot guarantee that." Anna said smiling.

"You can _never_ guarantee that Anna." Castiel said with a sigh. Anna handed him her half of the pizza cost then Castiel hurried downstairs to retrieve the pizza. He hoped that the film Anna picked did not include a certain Dean Winchester because Castiel had had enough of that guy over the weekend to last him a lifetime.

* * *

Notes: Thank you to all of the really positive feedback I've received from this, it really does mean a hell of a lot to me to know that you guys are enjoying this so far. I'm looking to update twice a week so the next update should be on Saturday/Sunday. Updates should be on Wednesdays and Saturdays from now on.


	7. Chapter Seven

**Chapter Seven**

Papers and magazines across America and countless websites were still talking about the 'Win A Date' competition, Dean and Anna even after a whole week. Dean couldn't go anywhere in New York without seeing his face all over the front page of far too many glossy magazines. He couldn't go anywhere without bumping into countless fans and it was starting to get to him. He'd never minded being in the public eye so much. When he was dating one of his co-stars from a film he had been in three years previous the media had gone insane over it but there was nowhere near as much publicity back then as there was now. Dean had several suspicions that Pamela was behind most of stories being printed.

Sam and Jo had been no real help apart from making countless jokes at Dean's expense. Normally he loved having Sam in New York with him but part of him was actually glad to see Sam go back to Palo Alto in the end because the constant piss taking was starting to seriously annoy Dean. Jo could clearly see this so she'd stopped once Sam had gone back to Stanford but now Dean could feel himself getting into a funk that he was sure would take a while to get out of.

* * *

"Maybe you should take a break or something like that." Jo said shrugging her shoulders as she made him a cup of coffee. Dean had dropped into the café where Jo worked to see her and complain that he was feeling like shit.

"Yeah, because Pamela would love that." Dean said yawning. He'd been up all morning at meetings with casting directors and he was exhausted even though it was only midday.

"What is really getting to you? Because it can't just be the press; they've been hounding you for years and it's never gotten you this annoyed before." Jo asked passing Dean his coffee. Dean shrugged because he wasn't sure if he wanted to mention to Jo that he was actually missing the person he felt like he was when he had been with Anna the weekend before. "Shit…it's not the 'Win A Date' girl is it?" Jo asked peering at Dean. Dean _hated_ that Jo had known him for so long that she could practically read his mind over certain things. "Oh holy shit, you're in_trouble_…you liked the 'Win A Date' girl _didn't _you?"

"Jo…"

"I'm not going to shut up Dean, if you like her then go and do something about it." Jo said bluntly.

"Yes because Pamela wouldn't mind me having a relationship with Anna." Dean said sarcastically.

"Well isn't she the one shoving all the stories in the papers?"

"Yes but that's for publicity to stop the whole 'Greenwich' thing from rearing its head." Dean explained.

"Are you ever going to talk about-"

"No I am not going to talk about it Jo." Dean said firmly.

"Um…excuse me?" a small voice asked from Dean's side. Dean looked at Jo as if to tell her to get back to work and serve the customer but Jo just smirked. Taking that as a hint Dean turned and saw a teenage girl smiling widely at Dean. "Hi…I'm really sorry to interrupt but…but could I possibly have an autograph? I'm a huge fan…" the girl said holding out a notebook.

"Um…yeah sure. What's your name?" Dean asked slipping into his charming 'actor' mode that Jo liked to take the piss out of all the time.

"Oh it's Katie." The girl said happily as Dean quickly wrote out a small message and signed the notebook.

"Hey Katie, how about I take a lovely photo of the two of you?" Jo asked smirking at Dean. Dean shot her a glare but then smiled back at Katie who just looked star struck. Katie nodded her head and handed Jo an iPhone while wearing an expression of awe. "Smile for the camera Dean." Jo said before she quickly took the photo of Dean with his arm around Katie. Once Katie was gone Jo couldn't stop laughing.

"I really hate you sometimes." Dean said glowering at her.

"Oh bite me Winchester and grow some fucking balls already. If you like the 'Win A Date' girl then go and do something about it. At least Pamela won't mind if you have sex with this person."

"You're a bitch sometimes Jo and her name is Anna." Dean said making sure he had his coffee before he said goodbye to a smirking Jo. He didn't want to admit it but maybe she was right, he should just grow some balls and do something about the fact that he hadn't been able to stop thinking about the 'Win A Date' night all week. "Pamela would kill me though. She'd be convinced that I was going to screw everything up."

"Don't tell her then. Say that you're going to go and see Sam over in California."

"I've never lied to Pamela before."

"You always lie to Pamela." Jo pointed out.

"Fine but-"

"No, you're going to wherever that Anna girl is from and you're going to grow spare, so help me God." Jo snapped giving Dean the firmest look ever. This was the look that she had inherited from Ellen and was the same look that Dean had seen for most of his childhood whenever he did something that had pissed Ellen off, like getting himself suspended from school for fighting though that had only happened once…ok maybe five times.

"You're bossy." Dean said pointedly to Jo.

"And you're frustrating. Now get out of here, I've got work to do." Jo said though she gave Dean a warm smile as he left.

* * *

Lying to Pamela turned out to be a lot easier than Dean thought it would be purely because Pamela knew full well how much Sam meant to Dean, she would never really complain about Dean leaving new York for a few days to visit Sam in Palo Alto and Dean was pretty damn thankful for that.

Discovering whereabouts in Chicago Anna lived in had also been easier than Dean originally thought. All it took was to distract Pamela long enough to have sneaking look into the files Pamela kept that were about the 'Win A Date' competition. Anna's entry, along with her address, had been right at the top so now as he turned up the volume of the Impala's radio Dean pressed his foot against the accelerator and he could feel the car's speed increase rapidly. The highway leading towards Chicago was relatively clear and Dean was enjoying the feeling of just_driving_. It had been too long since he'd just been out on the road though throughout the journey so far Pamela had kept up a steady stream of messages.

**Pamela Barnes: **_How long are you going to be in Palo Alto for? There's a meeting with the _Diversion _people next week. I'm not sure if you'll be needed there yet._

**Pamela Barnes: **_Don't do anything stupid in Palo Alto. The publicity from the Win A Date is still going strong._

**Pamela Barnes: **_ And by stupid I mean that you go out and get drunk with your brother thus ending up in the papers for looking like a complete and utter drunken idiot._

**Pamela Barnes: **_Oh I've gotten you an interview in _UK Vogue_. They want to shoot in two weeks. Don't do anything stupid like get a new tattoo in that time like you did when you had that _GQ _shoot._

**Pamela Barnes: **_For your interview with Jimmy Fallon in two weeks you're wearing a Gucci suit as requested by the designer and for your interview with _Good Morning America! _I'm currently arranging outfits with a stylist. Don't demand to wear ugly ratty shoes like the last time._

**Pamela Barnes: **_Don't forget you have an interview with next Monday!_

**Pamela Barnes: **_You better be driving because if you're just ignoring these messages to piss me off then I'm going to butcher you._

After the last text Dean had put his phone on silent and had just turned up the volume of the radio even more. Led Zepplin blasted out and for the first time in ages Dean felt truly free. He knew he could only ignore Pamela for so long before she went into a fit of rage but until that time Dean was going to enjoy the silence and pretend that Pamela didn't exist for once.

By the time he got to Chicago it was around ten in the evening, windy and freezing cold. Living in New York had made Dean used to the freezing cold weather but still, he actually wouldn't mind a trip to California now if it meant that he could see some sun for once before the summer. After about ten minutes for searching for the right street he spotted the apartment building that Anna lived in and there was no turning back. Here went nothing…

* * *

Dean knocked on the apartment's front door hoping that this was the right place otherwise he was going to feel like a total jackass standing in front of some random person asking about where Anna lived. He heard shuffling coming from inside the apartment then the door opened to reveal not Anna but a messy haired Castiel wearing a University of Chicago hooded pullover and jeans. Was Dean destined to have only Castiel answer doors or something? Judging by Castiel's both shocked and vaguely annoyed expression Dean was the last person he thought he would be opening the door to.

"Well at least I got the right apartment first time round." Dean Winchester said and instantly regretting it because there were probably a hundred other things he could have said instead of that.

"What…what are _you _doing here?" Castiel asked looking utterly bewildered. Dean couldn't blame him to be honest. He doubted that Castiel and Anna had actors appear at their apartment doors every night of the week.

"I came to see Anna." He said. For the entire drive here Dean had been thinking about seeing Anna and yet now he was relieved that it had been Castiel to open the door even if Castiel was the Milton sibling that clearly disliked him. There was something about this scruffy and scowling guy that intrigued Dean and Dean had to admit that he had found himself thinking about Castiel from time to time over the past week or so. He had made sure not to mention that to Jo in any way, shape or form.

"Yeah well that's the general feeling around here most times." Castiel muttered. "Anna's not here at the moment but I'm not going to be a jerk and make you wait in the hall." Castiel said turning back into the apartment. A shadow of a smile fell across Dean's lips as he remembered Castiel saying something along those the first time they had met at the hotel. "That was a cue to come inside in case you didn't realise that." Castiel said when he looked over his shoulder and saw that Dean was still standing in the doorway. Dean quickly hurried inside and shut the apartment's front door. Castiel had clearly been working because a laptop was on the couch surrounded by a few old looking hardback books and a notepad covered in notes. Several half-drunk cups of coffee sat on a coffee table near the couch.

"I'm sorry if I interrupted you. You're not working on anything are you?" Dean said nodding at the laptop.

"No not really so don't burden yourself with worry about it; all I was actually doing was postponing the definite writing of a paper of mine that is due in three days." Castiel said motioning for Dean to come into the main area of the apartment. There was a small yet very tidy kitchenette to the side that had the cleanest looking stove ever. Either Anna and her brother were clean freaks or they rarely cooked. Judging by the amount of take-out menus stuck to the fridge it was the latter.

"So...this is where you and Anna live...it's nice." Dean said looking around the small apartment. It was a modest looking place but the bookcase near the TV held more books and DVDs than Dean thought physically possible.

"Well it's not movie star nice but it's decent" Castiel said with a shrug picking up a few of the coffee cups and taking them into a small kitchenette on one side of the apartment.

"I didn't mean it like that man" Dean said hating the fact that this guy made him feel nervous and like he was saying things he didn't mean to say.

"Oh I know." Castiel said smirking at Dean for a moment before he turned away. Dean was going to ignore the fact that his stomach jolted when Castiel smirked at him because that was too much to think about right now. Instead of looking at Castiel he turned to look at the large bookcase near the TV. Well-read and worn looking books and DVDs were fighting a battle against one another for space. There were countless titles that Dean owned himself with both the books and the DVDs as well as titles he had never heard of. Dean remembered that Castiel was a fan of Vonnegut and wasn't surprised to see all of Vonnegut's titles on the shelf. Then Dean noticed several of the film titles underneath a cluster of books.

"Wow, sweet movie collection here. Both the original and the remastered versions of _Star Wars_, the extended editions of _Lord of the Rings_…nice." Dean said whistling. "Anna had good taste."

"Those are mine actually. Anna's collection contains a lot less taste and a lot more you. Although the PBS _The History of Art_ box set belongs to Anna, she's watched it far too many times if I'm being perfectly honest." Castiel said. The piss taking coming from Castiel was a whole new experience for Dean, apart from Jo and his brother he had never met anyone who made joke at his expense when it came to his films. "Anna is probably going to be a few hours at least as she's with her friend Ruby so do you want to grab a drink or something? There's a quiet bar down the road that I sometimes go to and if I carry on looking at my laptop screen or that stack of books then I might go insane…or actually write something which would be even more insane." Castiel said surprising Dean because up until that moment he was convinced that this Castiel guy really disliked him and spending time with Dean was the last thing he wanted to do in the world.

"Um yeah sure." Dean said.

"Ok, let me grab my wallet then we can go." Castiel said walking into one of the small looking rooms off from the kitchenette. Dean went back to looking around the room and was drawn to a large photo on top of the bookcase. Anna and Castiel stood with their arms around one another and a younger looking blonde kid was on Anna's other side grinning mischievously at the camera. Dean assumed this was their younger brother Gabriel whom Anna had mentioned during their dinner in New York. Anna and Castiel looked about eighteen in the photo and the blonde kid looked about thirteen. All three of them looked so carefree and happy with wide smiles on their faces. Dean noticed that there were no photos of Anna and Castiel's parents, all the photos in the room were of Anna with friends or with Castiel and of Castiel with Anna or with Gabriel. It reminded Dean of his own apartment that was full of photos of him with Sam or Jo but hardly any of his parents.

Dean heard Castiel come out of his room and quickly turned to look at him so Castiel wouldn't think Dean was snooping around the apartment. Though Castiel wouldn't have noticed either way as he was busy shoving a wallet into his back pocket. "Ready?" Castiel asked Dean finally looking up. Dean had forgotten how freaking _blue_ Castiel's eyes were.

"Yeah sure, where is this bar we're going to?" Dean asked after a moment. He didn't mind going out but he wasn't keen on going to place that was full of people who could recognise him seeing as he had lied to Pamela about where he was going and had told her that he was going to visit Sam at Stanford in Palo Alto.

"It's a really small place and I guarantee no one there will know who the hell you are." Castiel said.

"Are you sure about that?" Dean asked warily. He wasn't too fussed about people asking for photos or autographs but Pamela would kill him if she found out he was really in Chicago when he had told her that he would be in Palo Alto.

"Oh I'm sure. Unless you were in some PBS drama or documentary about eighteen century literature or the history of Renaissance painters then I doubt anyone in the bar will even know of your existence." Castiel said with a slight smirk still on his lips.

"No, I've never been on PBS." Dean said.

"Oh I _know_; you _really_ don't seem like the PBS kind of guy. You're going to be completely safe from detection and fan adoration but if that gets too weird for you we can always find some sorority sisters who no doubt worship the very ground you walk on." Castiel said smiling at Dean yet again with a mocking smirk. If this was Jo or Sam saying this then Dean would have called them a 'bitch' and then swiftly told them to go to hell but he didn't want this Castiel guy to hate him more than clearly did already so he refrained from saying anything. Then Dean realised that he shouldn't have to worry if some random guy from Chicago hated him or not, why should he care so much? He really had to stop himself for a moment and remind himself that the last time he did anything to do with a guy it he landed him in hot water with Pamela and it was the reason he'd been made to this whole 'Win A Date' thing in the first place. Wait, where had that thought come from? He wasn't planning on doing anything with Castiel and he was sure Castiel wouldn't let him either way. He didn't even know what team Castiel even played for. Then again from the way he looked Dean knew Castiel wouldn't have to worry about either sex finding him unattractive. "Shall we get going then?" Castiel asked nodding towards the door and tearing Dean away from his confusing inner monologue.

"What? Oh yeah, sure. Let's go." Dean said.

* * *

The bar turned out to be a small dive of a place that was hip enough to have stacks of books all over the place and play music that Dean had never even heard of. It had that unkempt feel to it even if it looked clean…sort of. Dean had to admit that Castiel was right; Dean doubted anyone here knew who he was and he found himself actually liking that. He could just sit, drink a beer and talk to Castiel…if Castiel actually wanted to talk to him that was. As they walked through the bar Castiel nodded at a few people and when they got to the bar he smiled at a lanky guy with short dark sandy hair that didn't look old enough to have graduated from high school let alone work in a bar.

"Hey there Castiel" The guy called waving a hand when Castiel walked towards the bar.

"Hey there Alfie, can we get two beers please?" Castiel asked the guy with a warm smile.

"Sure thing man, is Anna not with you tonight?" The guy Castiel called Alfie asked sounding eager.

"No, she's out somewhere with Ruby tonight and the least I know the better." Castiel said grimacing slightly though still smiling. "Oh Alfie this is Dean, Dean this is Alfie." Castiel said motioning to both Dean and Alfie. Alfie gave Dean a genuine smile and it was clear he didn't recognise Dean at all. It was a happy feeling that Dean could get used to actually.

"Nice to meet you Dean." Alfie said smiling as he grabbed two bottles of beer. "You two have a good night and say hello to Anna for me." Alfie said to Castiel.

"I will Alfie." Castiel said nodding his head. Castiel led Dean through the bar until he found a small booth. The pair of them sat down and Dean looked around the bar. Despite the fact that it looked like the floor had never been cleaned properly and natural daylight was not something you easily find Dean thought it wasn't a bad place at all. In fact it reminded him of Ellen's, Jo's mom, bar back in Kansas. "One day Alfie will get over his undying love for my sister but today is not that day. I doubt any day this year will be that day either." Castiel said more to himself than Dean but Dean still found himself smiling. When Castiel wasn't giving him that unnerving stare that made Dean feel uncomfortable he was actually quite amusing.

"He hardly looks old enough to drive let alone work in a bar." Dean said chuckling. Castiel looked up at Dean and grinned back.

"Yeah, Alfie does suffer from having a serious case of the 'baby face'. You wouldn't believe he was actually twenty-one." Castiel said.

"I wouldn't even believe he's eighteen." Dean said.

"The baby face is one of the many reasons why Anna won't date him actually." Castiel explained. "Well that and his full name."

"Oh?"

"It's Samandriel Alfred, you can understand why he prefers Alfie. The poor kid "

"If it's any consolation towards Alfie I was named after my grandmother Deanna."

"Oh I know. That's just one of the many, _many_ titbits Anna knows about you and has 'fascinated' me with over the years." Castiel said darkly as he rolled his eyes. Dean stopped grinning and saw the small frown on Castiel's face. Like that the feeling of content disappeared.

"I'm getting the sense that you really don't like me very much." Dean said. Castiel gave him a surprised look but then gave an agreeing nod.

"Your perceptions of deduction are actually stellar. Ok, no I don't really like you…I didn't really like you. Then again the only insights I had into who you were came from Anna's endless supply of gossip magazines lying around the apartment…oh and those shitty E! News interviews that Anna has clogging up the TiVo." Castiel explained.

"God, now I feel really sorry for you for having to watch those fucking things. I hate doing those damn interviews. I never know what to say and I hate talking about my family life so I always come across like a great big tool." Dean said. He sipped from his beer and looked away from Castiel because the way Castiel was looking at him was making Dean nervous. Those fucking blue eyes were really intense.

"You certainly come across as less of an ass here than you do in interviews." Castiel said shrugging.

"Well that's a good thing I guess." Dean said grinning and he hated that his stomach jolted when Castiel grinned back.

"You're certainly surprising. You're less of an ass than I thought you would be which is a good thing considering my sister likes you and you came all the way to Chicago just to see her." Castiel said smirking. "Plus knowing that you've read and that you like Vonnegut makes you seem like less of a moron." Castiel added with yet another very thinly veiled insult towards Dean.

"Well then hearing that someone doesn't think that I'm an ass or a moron definitely makes up for the drive here." Dean said.

"Wait, you _drove_ all the way here from New York city?" Castiel asked raising his eyebrows. "Isn't that like a twelve hour drive?" Castiel asked furrowing his brow.

"Yeah give or take thirty minutes depending on the traffic leaving the city but I really love the drive plus I'm not that great with flying if I'm being perfectly honest." Dean explained scratching the back of his neck nervously. Just talking about flying made him feel nervous sometimes even though that made him feel like a complete wimp.

"Really? But you're an actor Dean; you travel all over the world. How can you be scared of flying?" Castiel asked raising an eyebrow before he sipped his beer.

"If man was made to fly he would have been given wings, it's as simple as that." Dean said and he was surprised when Castiel chuckled. "I try not to think about it too much when I have to fly abroad. Normally I always have some good music and a really distracting book. When I have to go to somewhere here in America I just drive. I like driving, when it's just me, a decent soundtrack and the road in front of me I feel so different from when I'm in New York or filming or at some award ceremony. When I'm on the open road I can pretend that my face isn't all over buses and trains in New York. I can pretend that I'm just some regular guy from Kansas driving down some random highway singing along, badly, to ACDC." Dean explained and he saw Castiel's face soften as he spoke. It was comforting to see Castiel's soft expression as it made Dean feel like less of the ass Castiel thought he was before.

"That sounds nice actually. Anna and I hardly ever drive anywhere. Everything we need is in walking or cycling distance or we just get the train. Whenever we go back home to Lincoln to see Gabriel we just get the train, we're only about two hours away from home." Castiel said before sipping on his beer.

"Man now _that_ sounds nice. Driving to Kansas or Palo Alto to see my brother is amazing, I really love it, but the drives can be really long." Dean said.

"I can imagine." Castiel said smiling slightly and it was amazing how different Castiel looked when he smiled. He didn't so…sarcastic or blunt.

"Yeah it takes nearly a day to get to Kansas and nearly two days to get to Palo Alto but my brother is worth it." Dean found himself admitting. God he never talked about his brother to people other than Jo and yet here he was sat in some random bar in Illinois talking about Sammy to some guy he really didn't know a lot about.

"Does your brother live in Palo Alto?" Castiel asked sounding genuinely interested in hearing about Dean's family and not in the infringing way that reporters or journalists normally did.

"Well he goes to school there; he's at Stanford studying to become a lawyer. We go back to Kansas to see family friends though and obviously we grew up there. My best friend Jo lived in Kansas up until a few years ago then she moved to New York and now she lives not too far from me. Her mom lives back in Kansas though." Dean explained. He hardly ever talked to people about his life back in Kansas unless he was asked in an interview and even then he never mentioned Bobby, Ellen or anyone else from his hometown of Lawrence. When he saw that Castiel was not only looking at him but smiling at him so much that the corners of his eyes were crinkled he found it difficult to look away.

"Wow, Stanford is a really good school." Castiel said sounding impressed. "Is your brother enjoying it there?"

"Yeah Sam loves it. He's got this great girlfriend that he's clearly crazy about and he loves the studying there so much. God he can talk for hours without stopping if you ask him about it which is great, the kid deserves some damn happiness." Dean said shaking his head slightly. God, he really never spoke about this sort of stuff, even to Jo sometimes, so it felt freeing to talk about Sam with the pride Dean really felt for his brother. He never liked mentioning Sam in interviews and he had a total blanket ban when it came to talking about his family history apart from growing up in Kansas.

"That sounds like Anna actually. If you get her talking about certain artists then she won't stop talking about them until you beg her." Castiel said with small chuckle.

"Funny, she said the same thing about you and authors." Dean said remembering how Anna had spoken about her brother during the meal in New York. Both Anna and Castiel spoke about each with fondness, it was clear to see that they were very close and it really did make Dean smile.

"She might have a point there if I am being honest. I can get very passionate when it comes to talking about authors." Castiel said looking a tiny bit shy almost.

"Who are your favourites?" Dean asked.

"You really want to know?" Castiel asked raising an eyebrow.

"Well you said that I seem like less of a moron now for liking Vonnegut so I'm genuinely interested." Dean said grinning slightly when he saw Castiel's surprise.

"Ok. Well obviously I love Vonnegut. Salinger is another one of my favourites as is Scott Fitzgerald. I must have read _The Great Gatsby _at least fifteen times when I was in high school actually. I've read a fair few Stephen King novels, then again who hasn't? I love the classics as well like Dickens and Hardy. There are so many amazing class novels out there and I think more people should read them. Oh and Hemingway! He's one of the greatest writers in American literature. I love Truman Capote as well, _In Cold Blood_ was pretty much a new genre when it was published and is such a great novel. Oh and Charles Bukowski is another incredible author." Castiel said and the passion in his voice made Dean smile widely because Castiel clearly loved reading so much. It was actually pretty adorable if Dean was being honest.

"Wow, Anna was right. You really love your books don't you?" Dean asked.

"Oh yes, I've read from a very young age. I've always loved to read just like Anna's always loved art and everything to do with it."

"I really didn't get into reading until I was a teenager. I mean I read to Sammy when he was younger. God he loved the _Harry Potter_ books. I read the first few to him and he couldn't get enough of them." Dean said still smiling at Castiel and he was glad when Castiel smiled back just as brightly. "I thought Sam was a nerd actually but you might beat him." Dean added.

"Your brother sounds like a really good person." Castiel

"Yeah…yeah he is. He's smart as hell and really going to go places." Dean said looking at Castiel and they both smiled at one another. Dean could feel a twinge in his stomach, it felt like something was actually pulling him towards Castiel and he couldn't shake it. Everything, from the fullness of Castiel's lip to the angular shape of his jaw drew Dean in making it impossible to look away.

A buzzing sound coming from Castiel's pocket broke the spell instantly though. Castiel looked away from Dean and down at his phone then drained his beer. "Oh, Anna is on her way back to the apartment, shall we head back there?" He asked Dean. Dean shrugged; he was actually having a good time with Castiel once they found some common ground. "I'll tell Anna that I'll be back in ten minutes or so. Her face when she sees you is going to amuse me greatly." Castiel said looking away from Dean and typing a message out on his phone. "Do you want to finish your beer?" Castiel asked without looking away from his phone.

"Urm, yeah sure." Dean said picking up his bottle and draining it of its content quickly.

* * *

Dean was actually quite sad that the walk back to Castiel and Anna's apartment from the bar was relatively quick. The weather was cold but in his leather jacket Dean didn't mind too much. Castiel kept up a conversation by pointing out places like a small café that he and Anna apparently went to a lot.

"I have enough early morning lectures to warrant drinking more coffee than most people put together." Castiel with a nonchalant shrug of his slim looking shoulders.

"What are you studying?" Dean asked once he realised he didn't actually know what Castiel was studying at university.

"My major is in English Literature." Castiel explained.

"Well I should have known what with all the books." Dean said with a slight chuckle.

"Yes, apparently most people can tell my major from a mile away." Castiel said wirily.

"Do you enjoy it?"

"Nine o'clock lectures can be brutal sometimes but it's nice to be getting a major for just reading some of my favourite books."

"What are you reading at the moment?"

"You're genuinely interested in knowing what I'm reading?" Castiel asked raising an eyebrow at Dean.

"Well yeah…" Dean admitted. He liked watching Castiel talk about books because of how passionate the guy became. There was something very adorable about it.

"We've just started reading _The Sun Also Rises_, it helps that I read it five times during high school."

"I've never actually read it." Dean said with a shrug.

"You should. Hemingway is a very good author. As I said, he's one of my favourites."

"I guess he would have to be seeing as you read his book five times."

"I re-read most books even if I didn't like it the first time round. I like to see if my opinion could be changed by life experience and sometimes I find that it is true. I can go from disliking a book I read at the age of fourteen to thoroughly enjoying it at the age of nineteen."

"Huh…maybe I'll have to try that with a few books I've abandoned in the past." Dean said.

"You really should. Opinions certainly can change over a varied period of time." Castiel said with another shrug of his shoulders before he stopped in front of a building and removed come keys from his pocket. They were back at the apartment building. Suddenly Dean felt nervous, he'd travelled all this way to see Anna and yet now he wasn't sure if he had made the right decision or not. What if Anna wasn't remotely happy to see him? "Are you coming Dean?" Castiel asked. Dean looked over at the guy, surprised that he had called Dean by his name and not something sarcastic like 'Hollywood Ken'.

"Um…yeah. Come on then." Dean said. They walked into the lobby which was completely empty of people.

"Most people are either out or back in their apartments by this time. This isn't a very lively building unlike other student housing" Castiel explained casually while they walked up the flights of stairs back to Castiel's apartment.

"No elevator?"

"Sorry Dean, you'll have to use those actor legs to something other than walking up and down a red carpet." Castiel said with a smirk. Well Dean might have walked into that one if he was being honest. They stopped climbing and soon came out into a hallway

A devilish laugh could be heard from inside Castiel and Anna's apartment even from out in the hall that sent a shiver down Dean's spine. That was a laugh that could probably be heard down in hell actually. Dean looked over towards Castiel questioningly and the look that Castiel gave him back was not at all helpful.

"Guard your loins." Castiel said with a sickening sneer across his lips. Dean was genuinely afraid of what was to come.

"Guard them against what exactly?" He asked warily.

"It's more 'who' than a 'what' and that 'who' would be the one and, luckily, only Ruby." Castiel said. Oh, Anna's best friend that she had mentioned back in New York. She couldn't be that bad could she? _Could she_? Castiel quickly unlocked the apartment door and Dean heard a whoop from inside the apartment.

"Cassie! Cassie can you come and make me a coffee? Anna's coffees are shit compared to yours!" Dean heard someone cry loudly. Castiel rolled his eyes and motioned for Dean to follow him into the apartment. Dean braced himself and breathed in deeply while he walked into the apartment.

"Cassie where have you…_holy shit_!" Someone cried when Dean walked into the apartment. "Oh sweet holy Hell, I'm fucking dreaming." The one apparently called Ruby said when she saw Dean walking in slightly behind Castiel. She had a devilish grin and long brown hair that hung wildly down her back. The look in her eyes was that of pure mischief. "Oh my…Anna…Anna…Anna!" Ruby yelled towards a closed door. The door opened to reveal Anna puling a hooded top on over her head. When the top was on she looked over at Ruby sighing loudly.

"What are you shouting about?" Anna asked. Ruby pointed at Dean animatedly causing Anna to finally look over to where Dean and Castiel had been stood. "Dean? My God, what are you doing here?" Anna asked staring at Dean with wide eyes.

"I came to see you." Dean said hating how pathetic that sounded and how it just didn't seem all that right now that he'd spent time and gotten to Castiel better.

"Damn, ginger gets all the luck." Dean heard Ruby mutter with a shake of her head.

"God…wow. It's great to see you." Anna said smiling happily while still looking surprised to see Dean here. She looked over towards Castiel who was wearing the same bored, mocking expression he always seemed to wear.

"Don't worry Anna; I kept an eye on Hollywood Ken for you and didn't corrupt him too much." Castiel said smirking. Dean's heart sunk when he heard to derisive tone in Castiel's voice, clearly their time was over. "If anyone wants me, which I highly doubt they do, I'll be in my room catching up on my reading." Castiel said going to the fridge, grabbing a can of soda then heading back towards the room Dean assumed to be Castiel's.

"Castiel-" Anna called but Castiel waved his hand to silence her.

"My good friend Hemingway is calling me Anna." Castiel said not looking at Anna, Dean or Ruby before he went into his room. Anna looked at Dean and chewed at her bottom lip while looking nervous.

"I'm really sorry about him; I hope he didn't give you too much shit." Anna said with a light yet nervous sounding laugh.

"Oh you know, he can be a little blunt and sarcastic but it's nothing I can't handle." Dean lied shrugging and Anna smiled brightly clearly not hearing the lie in Dean's words. Dean didn't really want to mention that he found Castiel kind of fascinating even if he was a bit sharp and normally insulted Dean without caring what Dean thought. If he was being really honest Castiel had mocked him most of the night but Dean really hadn't actually minded after he'd gotten more used to it, he'd found it refreshing and he'd found Castiel refreshing yet now it was making his reasons for coming here to see Anna only more confusing.

"That's good." Anna said happily.

"Well I hate to ever follow Cassie's example when it comes to _anything_ but I'll be heading off as well. If I'm not the centre of attention in a room I tend to turn murderous." Ruby said flipping her hair dramatically.

"She's joking." Anna said reassuringly to Dean.

"Only slightly." Ruby said winking at Dean. "You folks have a nice night." Ruby said winking at Anna then Dean before she strolled out the apartment. As she was closing the door Ruby gave Dean a flirtatious smirk. It was truly terrifying.

"So that was your friend Ruby…" Dean said raising his eyebrows.

"Yeah, I'm sorry about her as well actually. She can be pretty blunt and sarcastic as well just like my brother…I seem to draw sarcastic people towards me like moths to a flame." Anna said before she shook her head and looked at Dean with disbelief. "I can't believe you're here though, it's such a surprise."

"Well I was back in New York and I kept thinking about everything you said to me and I realised that I needed to talk to you again." Dean said and he couldn't help but smile when he saw Anna's face light up.

* * *

Castiel swiftly shut his bedroom door and swore to himself as he marched over to his bed. What the hell had happened tonight? One moment he was ignoring the essay he needed to write and the next moment he was inviting _Dean Winchester_ out with him. Not only that but he was_talking_ to Dean Winchester and not just mocking him. He was enjoying talking to Dean Winchester as well, he had enjoyed the company they had shared and he'd been surprised that Dean was less of a moronic dickhead than he thought. Dean was actually quite a decent and interesting person if Castiel overlooked the fact that Dean had driven for over twelve hours to, no doubt, try and get into Anna's pants. Apart from that Dean was a decent guy who clearly cared about the people around him…the only real downside to him was that he was a shitty actor who had been in some truly terrible films…oh and he was straight…

Not that Castiel cared about that…much…

"Shit" he muttered to himself as he grabbed for his worn copy of _The Sun Also Rises_. "I'm in trouble…"

* * *

Castiel woke in the morning groggy and annoyed. He hoped more than anything that nothing had gone down between Anna and Dean, he was glad that he had gone to sleep with his headphones in as hearing his twin sister potentially have sex with Dean Winchester was not something he wanted to hear. It wasn't just because hearing his sister having sex was not something he wanted to hear anyway it was because it would be with Dean Winchester, a guy who, up until several hours previously, Castiel had thought a completely egocentric moronic ass with zero talent. He still thought Dean Winchester had little talent; Castiel had after all been made to watch all of the guy's films, but knowing that he was actually smarter than Castiel had thought and very family orientated had slightly changed Castiel's view of Dean. Castiel wasn't sure if this was a good thing or not. The safest thing to do was to simply shove earphones into his ears, turn the volume on iPod up as far as it would go and hope that steady guitar music would help him to forget everything that had gone on during the evening. Actually not thinking about Dean full stop would have been more helpful as now the lines were beginning to become a little murky.

Castiel dragged himself out of bed for his crack of dawn lecture without and real motivation purely because it was so early. He walked out of his room and into the main area of the apartment in search of much needed coffee. Stretching out with a yawn he went over what he needed to do that day and was about to walk to the kitchenette to make said coffee when he noticed someone lying on the couch fast asleep and looking relatively peaceful.

Dean Winchester did not look like the millionaire film star he was when he was asleep. He looked like some regular guy, someone who Anna could have picked up at a local bar without a dollar to his name. He looked…peaceful actually. He really didn't look like the conceited asshole Castiel had thought he was the day before. The night before had made Castiel see this guy in a completely different light but that really didn't matter now because Dean was here for Anna. Last night it was clear that Dean was here for Anna and Anna alone so it didn't matter what Castiel thought of Dean in the slightest right?

Shaking his head Castiel tried to distract himself by making a large mug of coffee but making coffee only took so long and it wasn't before too long that he was stood near the end of the kitchenette, sipping coffee and watching as Dean slowly breathed in and out, looking at ease and very tranquil while he slept. This wasn't helping matters at all so, after telling himself to grip of himself, Castiel slammed his coffee mug on a nearby surface and ran his fingers through his permanently messy hair.

"Cas…Castiel?" he heard someone mutter. Turning back towards the couch he saw Dean opening one bleary looking eye.

"Oh…sorry if I woke you." Castiel said quickly. He needed to get going…now.

"Were you watching me sleep?" Dean asked rubbing sleep from his eyes.

"Hardly, I just came in here to make some coffee and noticed you were in here. I would hardly watch you sleep, I'm not some crazy Dean Winchester fan." Castiel said with a snort. He grabbed his mug, gulped the last dregs of his coffee and went to turn away from Dean but a thought went through his head and he couldn't stop himself from asking Dean a question despite him wanting to get the room as soon as he could. "What exactly are you doing sleeping on my couch?"

"Oh well I just drove here and forgot to book into a motel or anything so Anna offered me the couch to sleep on." Dean said sitting up and stretching out his arms "Actually it's damn comfy, better than some crappy motel mattresses I've slept on in my time." Dean explained between loud yawns.

"Yes, you look like a regular motel patron." Castiel said sarcastically.

"Actually when I was first auditioning for roles I spent a lot of time staying in shitty motel rooms." Dean said frowning slightly and Castiel felt strangely proud that he had gotten a rise out of Dean even if was a bit of a jackass move.

"Well, Hollywood Ken, there are fresh towels, enough mini shampoo bottles stolen from upscale hotels thanks to Ruby's kleptomania and even a coffee making facility, also known as the coffee maker, so you can pretend this is a lovely motel with all your Hollywood Ken needs. Oh just don't eat the Apple Strudel Pop Tarts in the cupboard, I've been living on Ramen noodles since New York and those Pop Tarts are my only luxury." Castiel said and before Dean could say anything Castiel strolled back into his room to grab anything he needed for his morning lecture minus his laptop and the reading material because that was back in the main room with a no doubt slightly pissed off or insulted Dean Winchester. True Castiel had started to like the guy last night but that wasn't going to stop him from mocking the guy, heck he could easily take it being a millionaire with his face plastered all over Times Square.

Castiel grabbed a jacket from the messy pile of clothes on top of his clothes hamper and shoved it on. He only had the class in the morning then his entire was free so he could finish off the paper he'd been neglecting. Knowing he only had to sit in a lecture for two hours wasn't too bad, at least the highly annoying girls who sat behind him would be too tired at nine in the morning to witter on about nonsense.

"Can you tell Anna that I have a lecture until eleven then I'll be back home?" Castiel asked Dean who just nodded. He probably thought that if he said anything else then Castiel would give him some snappy comment. It was tempting but if Castiel stayed around for too long antagonising a movie star then he would be late for his lecture and end up having to sit at the back with the stoners who would do nothing but sleep or watch _Family Guy_ clips on their laptops. "Thanks" Castiel said appreciatively as he picked up his laptop and books then shoved them into his messenger bag. "Oh if you do need to use the shower or anything like that then do go ahead" Castiel then said just because he felt like he needed to be less of a dick towards Dean until he thought up more snappy insults to throw Dean's way.

"Thanks man." Dean said giving him a quick smile. Castiel felt obligated to return it before he hurried out the apartment.

* * *

**Author's Note: **

**Well I certainly didn't mean for this chapter to be more than 8,000 words…ooops. Oh well, I regret nothing.**

**You guys have no idea how much research I did for this chapter just to find out where places are in America, how far they are from one another and how long it would take to drive to places. I should have set this fic in the UK then I would at least know where places are! Then again I was convinced that Bristol was by Cornwall/Devon…it's not, it's by Wales. Oh well, it's not like I took a geography GCSE and thought India was in Europe (unlike one of my friends). **


	8. Chapter Eight

**Chapter Eight**

Seeing as he'd driven for twelve hours the day before Dean thought he was in need of a damn good shower. The bathroom was only small but at least the shower worked. Castiel was right when it came to miniature hotel shampoos; the bathroom cabinet was full of them from various hotels across America. Dean grabbed a small bottle of shampoo and had a shower that gave him time to think. He was here in Chicago and now that he was here he was going to try and figure out what he was actually going to do. He had felt a connection with Anna during their dinner in New York, he had found her interesting and she was someone he could easily be himself around. However there was Castiel, the derisive and intelligent Castiel who mocked Dean at every opportunity he got and clearly had thought of Dean as an egotistical moron up until the night before. He also probably disliked Dean even if he didn't think of Dean as an ass anymore. Most importantly he was a guy. Pamela was going to kill Dean if she found any of this out. Thank God she thought he was in Palo Alto.

After about nearly an hour of standing in the shower Dean decided that he needed to stop thinking about what the hell he was doing in Chicago and get the hell out of the shower before he became all wrinkled. He was getting dry and changing back into the clothes he had worn the day before when he heard his phone ringing. Checking the caller ID he saw that it was Pamela. She was probably pissed because Dean hadn't text her back from the day before. Before picking up his phone he grabbed a towel and began to dry off his hair as he answered the phone.

"Hey there Pamela. Look, I'm sorry for not texting or calling you back yesterday and everything." Dean said quickly before Pamela could get the chance to yell at him.

"Dean, where exactly are you?" Pamela barked as soon as Dean had finished talking. Dean winced because Pamela sounded incredibly pissed off and that was never a very good thing.

"You know where I am Pamela. I'm up at Stanford with Sam." Dean lied smoothly as he towelled his hair dry. Walking out of the bathroom Dean moved into the main area of the apartment and placed the towel onto the nearest chair to him. Castiel had told him to make himself at home, as long as he didn't eat any of the Pop Tarts, so now Dean was looking through kitchen cupboards for something edible. Though apparently the only things Anna and Castiel ate apart from take-out were Ramen noodles, Lucky Charms, Pop Tarts and Jelly Beans. Dena was seriously wondering how the hell Anna and Castiel were even still alive. Sam would have a heart attack just looking at this food.

"Oh really, you're up at Stanford? How long have you been there for?" Pamela asked sounding very suspicious.

"I've been there since yesterday Pamela, are you going crazy? Maybe you need a good vacation or something like that." Dean asked rolling his eyes heavily.

"Don't start with me Dean." Pamela said sighing loudly "So you're really at Stanford then I suppose these photos of you leaving a random bar in Chicago that were sent to me at six this morning are all fakes then?" Pamela asked sounding furious. Fuck, so much for Pamela thinking that Dean was in Palo Alto after all then. Dean braced himself to the shit storm Pamela was likely to throw his way. "What exactly are you doing _Chicago_ of all places Dean? And don't try and lie to me because I will find out the truth in the end even if it kills me…or you." Pamela said sounding incredibly threatening.

"I was seeing Anna and Castiel." Dean admitted because lying to Pamela right about now didn't seem remotely sane or smart, it was just easier to tell her the truth even if she did shout at him.

"Anna and Castiel who?" Pamela asked.

"Anna and Castiel Milton…" Dean said wincing slightly because he knew what was coming.

"The _'Win A Date'_ girl? You travelled all the way to _Chicago_ to see the _'Win A Date' girl_ and her _brother_? Oh for all that is holy! Dean I told you _not_ to _sleep _with her!" Pamela hissed.

"I haven't slept with Anna" Dean said quickly. "So please stop panicking Pamela." Dean added sighing loudly. He gave up on searching for something to eat and grabbed the slightly wet towel he'd placed on the nearby chair. He took the towel back into the bathroom and rested against the shower door because talking to Pamela was beginning to exhaust him.

"I'm Dean Winchester's agent and publicist! It is _clearly_ my job to panic because that's the_ only_ response to give the things you do!" Dean heard Pamela yell down the phone. He might as well sit down because she was clearly gearing up to yell at him for some time. "Remember the time when you were going to elope with that idiotic supermodel Lisa Braden? Then there was the time you disappeared for three days with that snarky indie actress Meg Masters. And _then_ there was the time with the singer Bela-"

"Yeah, yeah I get the picture Pamela." Dean said sighing loudly. He really wasn't up to hearing Pamela list every single one of his flaws at that moment and Pamela's yelling was beginning to give him an almighty headache. "Look, I'll be back in New York in a few days at the most ok?"

"But Dean-"

Jesus Christ Pamela, I'm not going to elope or run away with anyone. I'm not going to do anything that will make you remotely freak out" Apart from staring too much at Castiel but Dean was not going to mention that to Pamela because that might send her over the edge and make her get the first plane to Chicago so she could either murder Dean or drag him back to New York as quickly as possible. "So please stop freaking out and if you hear anything about that film then please call me ok?" Dean then said while he heard Pamela huff on the other end of the phone.

"Dean I really don't think-"

"Goodbye Pamela" Dean said hanging up on Pamela and feeling relief surge through his body but that was only brief because knowing that Pamela was freaking out over him always made Dean feel bad in the end. God Dean needed coffee more than anything right now. Walking to the kitchenette Dean set about making himself a mug of coffee but had to stop after a moment when he became too discouraged by Pamela's annoyance at him and the fact that he couldn't even go out somewhere without someone taking a photo of him. Dean was rubbing his eyes in frustration when someone came out of one of the bedrooms. Thinking it was Anna, Dean looked up and was surprised when he saw Castiel.

"Is everything ok?" Castiel asked walking to the kitchenette. Dean wasn't sure how long Castiel had been back from his lecture but it didn't look like long as he still had his jacket on. It was surprising to hear how worried Castiel sounded. He sounded so sincere without any of the mocking tone Dean was quickly getting used to, just like he had the night before in the bar. "I wasn't eavesdropping but I heard you on the phone and you seemed pretty pissed."

"Yeah, yeah I'm ok. It's just my agent/publicist having a heart attack over where I am because I told her I was going to see my brother at Stanford instead of coming here. It's fine though, she lives to panic about me." Dean said shrugging.

"Well it's a way to make a living I guess." Dean heard Castiel mutter and Dean wasn't sure if it was an insult or not. "Do you want a coffee or something?" Castiel then asked Dean holding up a mug invitingly.

"Yeah, thanks man. That would be really good actually." Dean said giving Castiel a smile which Castiel returned after a few moments.

"I picked up some bagels as well. I realised when I went to my lecture that there is basically nothing in our cupboards." Castiel said pointing to a brown paper bag.

"Yeah…you and Anna rally don't do cooking do you?" Dean asked.

"No, if there weren't so many great take-out places around here then I think we would starve or die from food poisoning." Castiel said shrugging while he made Dean a mug of coffee. Dean reached over to the bag of bagels and quickly helped himself. "Both of us have learnt from the incident of Thanksgiving 2009." Castiel said warily.

"That's sounds…ominous." Dean said narrowing his eyes slightly.

"Anna and I were in charge of cooking the turkey." Castiel said. Dean let out a low whistle. There were far too many things that could go wrong with the Thanksgiving turkey.

"How badly did you fuck it up?" he asked and Castiel actually winced. God that poor turkey must have suffered.

"The poor thing was burnt on the outside and raw in the middle." Castiel said and Dean couldn't help but burst out laughing. "That just one of the many stories that proves the theory that Anna and I should never be in charge of cooking. I can handle Ramen noodles because they're impossible to fuck up but that is about it."

"Yeah, because you get so much nutrition from Ramen noodles and Jelly Beans."

"The Jelly Beans are Anna's. For future reference they are the quickest way to her heart." Castiel said. With that comment Dean swiftly remembered why he was here, that he'd come here to be closer to Anna and the way she made Dean feel. "Then again I'm sure that driving four twelve hours straight and turning up out of the blue could also be a swift way to her heart." Castiel added with a shrug.

"Yeah…look I'm sorry about just turning up here and camping out on your couch." Dean said after a few moments of silence. Castiel looked up and gave Dean an odd look that he couldn't really place before he shrugged his shoulders nonchalantly

"Look Winchester its fine, you don't watch endless episodes of _Cupcake Wars_, eat all the cereal and Pop Tarts or drink all of my organic mango juice so you're actually better than Anna or my brother Gabriel at this moment in time." Castiel said handing Dean a mug of coffee.

"I can safely say that I have never seen an episode of _Cupcake Wars_." Dean said feeling rather proud of himself considering he did watch an awful lot of shit television thanks to both Jo and Sam.

"Well then I've just gained a small percentage of respect for you." Castiel said.

"So what's the percentage now?" Dean asked giving Castiel a grin that most people would have taken as flirting. Maybe that wasn't the greatest idea but Dean didn't really care because Castiel probably wouldn't even notice or care. Right?

"Oh it's about one per cent now." Castiel said but he said it with such a mocking but bright smile that Dean couldn't feel offended in the slightest. Instead he chuckled then took a sip of his coffee.

"Fuck me, this is good coffee." Dean muttered because _damn_ it was good coffee. Castiel had a freaking talent.

"Well it's nice to know that my coffee could get me laid." Castiel said as a slow smirk grew across his lips. His eyes were dancing with a silent chuckle and Dean couldn't help but just watch him smile because it seemed so relaxed and natural. Dean had made him smile like that and it felt good, it felt great actually.

"I think the looks you give people could get you laid to be honest Castiel." Dean said before he realised what he had actually said. Castiel raised an eyebrow questioningly. "You have a pretty intense way of looking at people" Dean said suddenly feeling slightly hot under the collar. Dean wasn't going to mention that the way Castiel sometimes looked at him could get Castiel laid. Fuck, this was entering dangerous territory. Anna needed to wake up and appear already so Dean could stop talking to Castiel.

"Well that's a useful thing to know that looking at someone could get me laid as well." Castiel said and he actually winked at Dean. Fucking hell... "Let's just hope it's not a talent that runs in the family or Gabriel will become a complete menace."

"I thought I was a menace already, wasn't that what evil Great-Aunt Rachel called me two Christmases ago?" A voice called from the main area of the apartment and Castiel spun round to look at the owner of the voice with a surprised look on his face. Dean saw the same skinny and mischievous looking teenager he'd seen in the photos that littered Castiel's apartment and quickly assumed that this was Anna and Castiel's younger brother Gabriel.

"Gabriel! What are you doing here? I didn't think you were coming to see us for a while. Wait…don't you have SATS that you need to be preparing for?" Castiel asked sounding slightly scolding.

"They're _months _away Castiel" Gabriel groaned loudly and rolling his eyes heavily.

"It's also a _Monday_ so shouldn't you be in school?" Castiel pointed out and Dean could hear the very familiar 'I'm the elder brother and I'm going to boss you about' voice that he used on Sammy all the time.

"The school was flooded over the weekend so we don't have to go back until Thursday." Gabriel said smugly.

"How did the school become flooded?" Castiel asked sounding very suspicious.

"The flooding of my dear sweet high school happened during an incident that did not at all involve me or anyone that I am in acquaintance with." Gabriel said sounding not at all convincing.

"If I get a phone call from Uncle Michael about you then I am going to be pissed." Castiel said. Now he just sounded like a mix between Ellen and Bobby whenever Dean used to get in trouble at school.

"You're not going…ok you _may _be getting a phone call from Uncle Michael." Gabriel said shrugging.

"I despise you sometimes Gabriel." Castiel said sighing wearily.

"You love me _really _Castiel. Now I want to hear all the news from Anna about her date with-" Gabriel started to say as he sauntered towards the couch until he stopped suddenly and stared over at Dean standing in the kitchenette. "Holy Jesus_ fuck,_ its Hollywood Ken." He said.

"I would tell you to mind your language but there's no point" Castiel said sighing.

"Um, Castiel...I don't know if you know this but the winner of Hottest Male and Best Actor in 2008, 2009, 2010, 2011 _and_ 2012 at the MTV Movie Awards is stood in your kitchen so I think I'm allowed to say 'Holy Jesus fuck'." Gabriel said in awe as he stared at Dean. "Dude, you were _epic_ in _The Extraction Point_! I must have seen that film _at least_ a hundred times! It was such a freaking awesome film!" Gabriel said animatedly. "Hey Cassie didn't you say that was the only Winchester film that was decent and that you actually enjoyed it?" Gabriel asked Castiel. Dean smirked when he saw Castiel go red and glare at Gabriel.

"You've been talking to Ruby too often you blonde menace and stop calling me Cassie!" Castiel snapped.

"_God_! Dude don't chew me out in front of _Dean Winchester_!" Gabriel groaned punching Castiel on the arm. "Wait...why the fuck is Dean Winchester in your kitchen?"

"Language Gabriel." Castiel said rolling his eyes and clearly not answering why Dean was here. Dean decided he'd try to save the situation by properly introducing himself to Gabriel.

"Hey man, I'm Dean. You're Gabriel obviously. Anna and Castiel have both told me a lot about you, it's really good to meet you." Dean said walking over to Gabriel and shaking his head. Gabriel looked pretty damn star struck by the whole thing for a moment before he started grinning mischievously.

"I hope it's been all good." Gabriel said winking at Dean. Dean heard Castiel groan loudly.

"Nothing about you is good Gabriel." Castiel muttered giving Gabriel the same mocking tone that he used on Dean. At least someone else was on the receiving end of Castiel's derision.

"_Dude_, not in front of the _movie star_!" Gabriel cried. "_Honestly_, if I'm going to get this treatment from my big brother then I'm going to find your female and nicer twin." Gabriel grumbled stomping towards Anna's room and opening it without knocking.

"What was-"

"Wait a second." Castiel said holding up his hand. "Three...two...one"

"Wait" Gabriel cried running back to where Castiel and Dean were stood. "If you're here then that doesn't mean that you're fucking my big sister does it?" He asked Dean. Castiel rolled his eyes and pointed Gabriel towards Anna's room. "_Fine_, I'll get the details from my _favourite_, nice and reliable sibling!" Gabriel said once again stomping into Anna's room and once again without knocking.

"And…that was my younger brother Gabriel." Castiel said smiling resignedly at Dean.

"Oh he's certainly something else." Dean said picking up his coffee mug and taking a liberal gulp because he felt he certainly needed it.

"That's the very polite way of putting it." Castiel said. "Most people would say he's a tricky little so and so."

"GABRIEL WHAT THE _HELL_ ARE YOU DOING IN MY ROOM?!" Dean and Castiel heard Anna scream. "Get _out _of my room! No don't sit down on my bed! Get _out now_!" She added sounding furious. Dean was about to offer his help when he noticed that Castiel was actually shaking with silent laughter. Dean could understand why he was laughing; sometimes it was better to just laugh than instead of shouting or getting annoyed. The amount of times that Dean found himself at Jo when she had annoyed him was actually ridiculous.

"So…you liked _The Extraction Point_?" Dean asked grinning at Castiel who was still laughing. Castiel straightened up and let out a few small chuckles before replying.

"I think my exact words after the four hours I spent in the cinema watching that films were 'Well that was actually tolerable and not a complete waste of my life' so you should take that as a compliment I guess." Castiel said with an indifferent shrug.

"That's the biggest compliment I'm ever going to get from you isn't it?" Dean asked

"Very much so." Castiel said smiling for a moment before he turned back to the sofa where he placed his laptop and a pile of notes onto the coffee table. Castiel was just picking up a pile of books when Anna came stomping out of her room with bedraggled looking hair and in just her pyjamas. Dean gave her a welcoming smile which she quickly returned until she turned to Castiel and glared murderously.

"Why is Gabriel here and more importantly why was he my wakeup call?" Anna asked Castiel sounding very annoyed.

"A good question to ask would be why you're only just waking up at eleven in the morning on a Monday." Castiel asked as he booted up his laptop.

"Because it is a Monday. I don't have any classes today and therefore I deserve some sleep. Now, why is Gabriel here?" Anna snapped.

"I have no idea." Castiel said shrugging. "He probably wanted the gossip about Hollywood Ken" Castiel added nodding over at Dean.

"God he's such a menace." Anna said before she smiled sweetly at her brother "Castiel…" she said almost pleadingly.

"No" Castiel said quickly.

"_Please_"

"No"

"Castiel! Please!"

"_No_" Castiel said firmly and Dean had to admit that he was slightly enjoying the show in front of him. If this was him and Sam then he would be expecting puppy eyes any second.

"Castiel please, please do this for me." Anna said and clearly she knew about the puppy eyes as well because she was staring at Castiel with the most pleading look Dean had ever seen on anyone except for Sam when he wanted to go to Disneyland and Jo when she want Dena to take her to a film premiere so she could meet Brad Pitt. "Just take Gabriel somewhere so he's out of my hair and not bombarding Dean with every single Winchester related question he and the internet can think up."

"May I remind you of the last time Gabriel and I spent time alone together. I was getting gum out of my hair for a week." Castiel said.

"How old was Gabriel?" Dean felt like asking.

"Oh this happened four months." Anna said smiling slightly though the look on Castiel's face was anything but happy. "Come _on_ Castiel." Anna said and Castiel sighed loudly.

"Christ…the things I do for you sometimes…you still need to repay me for the last thing I did for you." Castiel muttered as he shot Dean a look before abandoning his laptop and getting up of the couch. With the look of a soldier about to run head first into battle without any armour or weapons he marched into Anna's room and after a moment Dean could hear low, slightly irritated voices.

"You and Castiel really weren't joking about Gabriel were you?"

"No, not really. I tend to tolerate him but not when he's my morning wake-up…and I've just realised I'm still in my pyjamas…this is slightly embarrassing." Anna said looking down at her pyjamas as her face reddened. "I'm going to get dressed and I'll grab some breakfast." Anna added sounding slightly nervous.

"There's a bagels on the side. Your brother picked them up earlier on."

"You had me at bagels." Anna said flashing a grin at Dean. "I'll be right back." She said hurrying into her room. After a moment Castiel came out the room practically dragging an annoyed looking Gabriel along with him.

"Have fun." Dean said and he couldn't help but smirk when he saw Castiel's incensed expression as he pushed Gabriel out the apartment's front door. For a moment Dean was actually sad to see Castiel go but when Anna returned and smiled sweetly at him he pushed that thought out of his head. Despite Pamela's annoyance at him for going to Chicago Dean knew that she would after he go after Anna than Castiel. After all, he had a 'reputation' to uphold according to Pamela.

"Well getting rid of Gabriel was a lot easier than I thought it would be. I'm amazed he actually went with Castiel though if he stayed here he would have driven you insane by asking inane and incredibly random questions about most of the films you've been in."

"I've been asked some pretty random and inane questions in my time so I wouldn't really mind."

"Oh believe me, you think you've been asked random questions but then you hear one of Gabriel's questions and you realise that every other question you've been asked is normal in comparison." Anna explained. "He's…well he's something else."

"That's what I thought."

"I wish I could say that you get used to it but you really don't. I'm still amazed with some of the stuff he comes out with."

"Castiel seems to have his own way with dealing with him."

"Yes that method is called 'Yell as loud as possibly while glaring and hope for the best.'" Anna said with a small chuckle. "Look, I really hope that Castiel didn't give you a hard time last night. Like I said, he can be...well…prickly around people sometimes. I swear he's lacking in social skills." Anna said while she made herself a mug of coffee

"Yeah...yeah he can be but it was fine..." Dean mumbled.

"Do you want a coffee?" Anna asked lifting up her own mug.

"I'm fine; your brother's only just made me one." Dean said holding up his own mug. As Anna made herself a coffee Dean noticed just how many different types of coffee there was in their cupboards as well as the large looking coffee maker on the kitchen counter. "So do you guys basically live off noodles and coffee or something like that?"

"Pretty much. Castiel and I have learnt that neither of us will ever be remotely domestic so we just make do with take-out, caffeine and stuff like that."

"Yeah, your brother mentioned Thanksgiving."

"Oh don't, that still gives me nightmares. The _looks_ my family gave me that day were horrible." Anna said shuddering. "But are you sure Castiel was nice to you? I'd hate to find out that he was a complete ass towards you."

"No, he was fine. Though I thought he was going to murder your friend when she called him Cassie." Dean said and Anna chuckled as she sat down opposite Dean.

"Yeah...I'm not sure if Ruby is secretly in love with my brother and it's an affectionate nickname or if she just loves to antagonise him by calling him Cassie. On Castiel's part I think he's just waiting for the right moment to hit Ruby over the head with a very large and very heavy book." Anna said. "Knowing Castiel is would probably be the complete works of Charles Dickens."

"So no declarations of love on Castiel's side then?" Dean asked with a slight chuckle because the thought of Castiel and the crazy, wild looking girl that Dean had met last night was actually highly amusing.

"Oh God _no_...Ruby really isn't my brother's type at all...he likes...well...personally I think he's ideal person is a fictional character. He lives in books most of the time, oh and ever ask on his thoughts of On the Road or you will be sat listening to him ramble for at least two hours...without him taking a single break." Anna explained as she threw a piece of bagel into her mouth. "He didn't bore you with an endless conversation about books last night did he?" Anna asked sounding slightly concerned. "He has a tendency to do that sometimes…actually he has a tendency to do that all the time."

"No…no it was fine." Dean said quickly.

"Good…God, I can't actually believe that you're here…it's pretty crazy to be honest." Anna said shaking her head. "I mean…you're here…in Chicago when only a few days ago you were in New York being Dean Winchester."

"I'm still Dean Winchester." Dean said.

"Yes but there is a difference to the Dean Winchester in New York and the Dean Winchester standing in my kitchen drinking from a mug with _The Great Gatsby _quotes on it." Anna pointed out. The main difference between those two Deans was that the Dean in New York was watched from under a microscope most of the time and he couldn't even blow his nose without it ending up on Page Six but the Dean that was standing in Anna's kitchen…well he was a regular guy, at least he could pretend he was. The Dean standing in Anna's kitchen wasn't just drinking coffee from a mug that clearly Castiel's and he didn't have to leave to go a meeting or an audition. He could spend the whole day just in this apartment with Anna talking about whatever he wanted. The Dean standing in Anna's kitchen was a lot freer than the Dean in New York. "I just can't believe you're here… I mean I'm nothing special Dean, why would drive for twelve hours straight just to come and see me?" Anna asked as she looked down away from Dean and focused on her hands.

"Anna you are someone special ok?" Dean said and Anna looked up at him with a disbelieving look. "Besides, you said things to me in New York that really resonated with me."

"Really?"

"Really, I mean it Anna. What you said really made me think and that's why I'm here. You made me feel like a different person when we were out together; I didn't feel like just some actor, I felt like a person." Dean said and the sincere smile that Anna gave him was electric. Despite Pamela's annoyance at him Dean knew that being here with Anna was the right thing to do…right?

* * *

"Dean freaking Winchester is right there in your kitchen and you're making me leave so you can push me around Chicago! This is worse than the time you got Uncle Michael to ground me so I couldn't go out with that really hot girl from my Spanish class!" Gabriel grumbled sounding very much like an incredibly cantankerous toddler.

"You will do nothing but annoy the poor guy and Anna doesn't really want you there at the moment. That means I've been given the task of keeping an eye on you." Castiel said making it clear that dragging Gabriel around Chicago while his sister flirted with Dean Winchester was not something he was particularly happy about. "Come on Gabriel, when was the last time Anna was actually happy when it came to a guy?" Castiel asked hoping that he could appeal to his brother's softer side…if he actually had one. Both Castiel and Gabriel knew how much Anna had been hurt in the past, especially with her ex-boyfriend and by the look that Gabriel was giving Castiel it clearly showed that he did have a softer side.

"Fine, _fine _you can drag me around Chicago so I don't pester Anna and Hollywood Ken but you're going to tell me everything about the date in New York, especially why a certain MTV Movie Award winning actor is here and most importantly why he's in your apartment eating bagels and drinking out of your favourite coffee mug." Gabriel said while Castiel hauled him down the road away from the apartment.

"I'm trying to figure out why you think I would tell you any of that." Castiel said.

"Because I'm your beloved brother." Gabriel said winking at Castiel. Well that was stretching the truth to breaking point. True Castiel loved his brother but Gabriel was such a menace at times that he drove Castiel to the edge of breaking point.

"That is really not a good enough reason at all Gabriel." Castiel said.

"Fine…because if you don't tell me then I'm going to come up with as many hilarious and slightly sexual anecdotes that I can think of to tell Aunt Rachel and Uncle Michael when I get back home…plus I won't give you back the $20 I stole out your wallet the last time I was here." Gabriel said smugly as he pulled a $20 bill out of his pocket. Castiel grabbed the bill and shoved it into his back pocket.

"See, this is why Anna and I refuse to come back home most of the time." Castiel said shaking his head.

"No it's not; I'm the best brother there is." Gabriel said smirking.

"Of course you are Gabriel, of course you are." Castiel said sarcastically.

"So…details." Gabriel said raising an eyebrow at Castiel "Why is Dean Winchester here, when did he get here and once again _why_ is Dean Winchester here?" he asked making it clear that he wasn't going to take no for an answer.

"He's here for Anna as a far as I can tell. That's what he told me last night anyway." Castiel said shrugging.

"So he has slept with Anna, I _knew_ it." Gabriel cried chortling loudly. "My sister has slept with a movie star…God I'm so proud of her" Castiel refrained from rolling his eyes heavily.

"Dean Winchester has not slept with Anna. For starters he slept on the couch last night."

"Wait…he slept on the couch, that same couch that I sleep on when I stay here? So he's been here in Chicago for more than twelve hours and neither you nor Anna bothered to text me and tell me that? God, you two are the worst siblings ever." Gabriel said sounding hurt. "Wait…Anna went out with Ruby last night so what did Hollywood Ken do when he got here?" Gabriel then asked.

"How do you know Anna went out with Ruby last night?" Castiel asked.

"Ruby and I happen to be frequent contact with one another." Gabriel said sounding very self-satisfied with himself.

"Oh God…" Castiel sighed. The thought of Ruby and Gabriel in frequent contact was enough to give Castiel nightmare's for a week.

"So what did Hollywood Ken do seeing as Anna was out?"

"Dean just turned up out the blue last night when I was working on my essay. Anna wasn't in and I was just staring at my laptop screen hoping that my essay would write itself so I suggested that we go to a bar or something." Castiel said shrugging. Gabriel stopped him and just stared at him for a moment before his eyebrows rose in surprise.

"_You_ asked Dean Winchester to go with you to _bar_? Did aliens invade your brain?" Gabriel asked. "Hello, is that Castiel? Boring and stuffy Castiel? Are you in there Castiel?" Gabriel called shaking Castiel slightly.

"Shut up Gabriel, it was easier than having him loiter around the apartment while he waited for Anna to come home."

"Yeah sure…at least tell me that you didn't go to that depressing intellectual place that your friend Alfie works in."

"I don't like anywhere else" Castiel said with a shrug.

"God…poor, _poor_ Dean Winchester…"

"Thanks Gabriel…"

"Oh you're welcome." Gabriel said proudly. "So what did you and Winchester talk about at this bar?"

"How do you know we talked?"

"Because there is nothing to do in that weird bar but talk and listen to mopey music" Gabriel said. "please don't tell me that you bored Dean Winchester with a conversation bout books…oh God, you did didn't you? Now I feel really sorry for the poor guy. Of all the things you could take to Dean Winchester about you choose books!" Gabriel cried with annoyance as he shook his head. "God, you really could have asked him anything, _anything_, like if that was really his ass in _Train Tracks To Albuquerque _or if it was a stunt ass."

"Why the fuck would I ask him that?" Castiel asked starting to get really annoyed by Gabriel. Anna knew how little patience Castiel had so why she thought that going around Chicago with Gabriel was a good idea was beyond Castiel. Also who asked a person if they used a stunt ass or not?

"_I_ would." Gabriel said proudly as he smiled smugly, no doubt because he'd annoyed Castiel enough to cause him to swear.

"I question sometimes how we are related." Castiel said shaking his head.

"So did you just bore poor Winchester with talk about books?"

"No…"

"I'll take that as a yes."

"He was genuinely interested ok! He asked me what I was studying here and I answered! It may shock both you and Anna but I do know how to have conversations with people about subjects, I know how to answer questions. He likes Vonnegut and technically he started the conversation about books so I really don't know why you're acting like I was the one to bore him senseless about books even though I didn't actually bore him. He seemed to enjoy himself at the very least."

"Wow you're getting defensive." Gabriel said raising his eyebrows.

"I am not getting defensive!" Castiel shot back even though he knew full well that he was getting defensive and it was blatantly obvious as well. Dammit.

"You _are _getting defensive Cassie. Jesus, anyone would think that you have the hots for Winchester or something" Gabriel said snorting loudly. Castiel glared at him until Gabriel stopped snorting. "It would make a change from the last person you liked. What was his name? You know the pseudo-intellectual poet that always used to hang out in the bar last year."

"He was not a pseudo-intellectual Gabriel and his name was Alex." Castiel snapped.

"That's what Anna called him so that's what I'm calling him…wait you didn't deny that you have the hots for Winchester…you _don't_ do you?" Gabriel asked peering at Castiel with a look of suspicion.

"I have no idea what you are talking about Gabriel and if you carry on spouting nonsense like that then I won't take you to the Navy Pier or give you the Dylan's Candy stuff we brought for you in New York."

"Ok fine! I'll stop talking about your crush on Winchester."

"Gabriel-" Castiel said warningly.

"_Fine_ but I still think you like him. You haven't said anything offensive about him for at least ten minutes and you actually enjoyed his company last night without killing him. I give it a week before you want to get into his pants."

"You're ridiculous." Castiel said shaking his head but inwardly cursing Gabriel because if he could see that Castiel might potentially like Dean then would Anna and, more importantly, Dean himself see it? Castiel was going to have to stop being so obvious…if he was being obvious to begin with that was.

"And you're in denial." Gabriel sang smugly. Castiel was very tempted to throw his brother off the pier once they got to Navy Pier but he resisted the temptation because he and Anna had made a pact to not kill Gabriel before he graduated from high school.

"I'm eating your candy when we get back to the apartment." Castiel shot back to Gabriel who looked horrified.

"I'm shutting up now" Gabriel said quickly and he even mimed zipping up his mouth for dramatic effect. Castiel couldn't help but roll his eyes though at least Gabriel would be silent for several minutes at least. "How long do I have to shut up for?" Gabriel then asked. Ok make that several _seconds_ at least.

Castiel becoming increasingly more annoyed but now it wasn't with Gabriel, it was with himself. He had said to himself that he wasn't going to be that nice to Dean Winchester because it was a lot easier but this morning he had found himself talking to Dean Winchester like any other person, he had found himself making coffee for the guy and even laughing along with him. Now as he walked along the street Castiel's thoughts were becoming more crowded by the notion of Dean Winchester. Not the Dean Winchester Gabriel was babbling about and whose face was splashed all over the nearby movie theatre, no Castiel was thinking about the Dean Winchester he had spoken to the night before and this morning in his kitchen. That Dean was easy, relaxed and actually quite humble. He loved his brother and enjoyed long car journeys because of his fear for planes. He didn't seem bored when Castiel talked about books and was interested in Castiel's university course. Dean liked how Castiel made his coffee. These were things that Castiel knew about Dean, not Dean Winchester but just Dean.

No, he needed to stop thinking about Dean. He needed to remember how much he'd disliked the guy before he'd gotten to know him slightly. He needed to remember that he thought Dean Winchester was a terrible actor whose movies Castiel had been dragged to on more occasions than Castiel would care to remember. Dean Winchester was just movie star from New York who was here to try it on with Castiel's sister right? That was all he was and yet…yet Castiel was sure that he was more. He had seen how relaxed Dean had been last night and how open he had been about his family, he really did not seem like the asshole Castiel had thought of him previously and that was certainly frustrating because it made disliking Dean a hard thing to do indeed.

* * *

By the time Castiel got back to the apartment five hours later he was exhausted. Once Gabriel hadn't gotten over his strop he had dragged Castiel all over the Navy Pier which had been packed full of tourists despite the cold weather. Castiel had agreed to a game of mini golf (that Gabriel won purely because he had cheater) but he drew the line at going on the large Ferris wheel because being stuck in a small place dangling from a great height with Gabriel was not something Castiel saw as fun.

Anna had text Castiel telling him that she and Dean were going out for something to eat so Castiel could return back to the apartment. Gabriel looked visibly annoyed when he realised that Dean wouldn't be in the apartment when he got back and didn't stop complaining until Castiel reminded him of the large amount of confectionary that had been purchased in New York that was currently waiting to be consumed by Gabriel. A high school senior should not have looked so excited by the thought of $80 worth of candy.

With the $20 Gabriel had so lovingly returned to him Castiel ordered some food and tried to plot his brother's murder while Gabriel complained, loudly, that Anna had gone out with Dean Winchester instead of staying in the apartment.

"It's like she doesn't trust me at all." Gabriel said as he threw himself down onto the couch.

"She doesn't trust you." Castiel pointed out. He turned on the TV and quickly held up his hand when Gabriel opened his mouth to speak. "_No_, I am not watching any _Cake Boss_ marathons." He said firmly. Instead of anything involving loud people making ostentatious cake, Castiel happily settled on a re-run of one of his favourite TV shows.

"What if Anna and Winchester do get it on?"

"Why are you asking me that?"

"Because I want to know what you think of it."

"I don't have any thoughts on the matter apart from disappointment that Anna would choose someone who makes such bad films."

"You liked _The Extraction Point_." Gabriel said haughtily.

"No, I tolerated that film." Castiel shot back.

"You just have terrible taste in films I've decided." Gabriel sighed.

"You've seen _Mean Girls_ over three hundred times. You cannot comment on film tastes when I know that little fact."

"_Mean Girls_ is cinematic genius that will go down in history as a masterpiece so shut your blasphemous mouth." Gabriel said looking truly hurt but Castiel's comment.

"I really worry about you sometimes Gabriel." Castiel said shaking his head. Their food arrived and they soon settled into a comfortable silence that was mainly due to the fact that Gabriel was eating and that seemed to be the only time that Gabriel ever actually shut up. Castiel was thankful of the silence actually

* * *

Dean and Anna retuned back to the apartment not long before eleven because Anna needed to get up in the morning for her lecture. Gabriel had off due to boredom at the TV show they had been watching and was starting to snore. Anna seemed visibly relieved by Gabriel's lack of consciousness when she and Dean returned.

"Hey, did you have a nice night?" Castiel asked looking up at Anna and avoiding Dean's eye because that was easier than looking at him.

"Yeah, we did. How was your day with Gabriel?" Anna asked.

"Tiring, you really owe me now. He made me play crazy golf on the pier." Castiel said. His voice hopefully told Anna his thoughts on crazy golf which was less positive.

"Oh God, I'll make it up to you Castiel, I promise." Anna said smiling at Castiel. "I'm going to go to bed otherwise I'll be falling asleep in my morning class tomorrow." Anna said before she turned to Dean with a warm smile. It was at this point that Castiel pointedly turned away and focused on the TV screen. Anna said something to Dean that Castiel couldn't hear and Castiel didn't look away from the TV screen until Anna walked up to him and draped an arm across him, hugging him quickly. "Thank you for today, it really meant a lot."

"It's fine Anna." Castiel said looking up at his sister and giving her a gentle smile.

"Night Castiel." She said kissing him on the forehead before she walked back to Dean. After a moment he heard Anna's bedroom door open then close. Castiel glanced over to for a moment and saw the easy smile he was beginning to get used to. Castiel really hated that smile. After a moment Dean yawned slightly.

"Tired?" Castiel asked.

"Sort of I guess." Dean said with a shrug.

"Yeah…Gabriel's no doubt going to commandeer the couch so you can sleep in my bed." Castiel said throwing a spare quilt onto the couch for Gabriel to use and it wasn't until he said that he realised that might have sounded like he was flirting. Shit, Dean didn't think he was flirting with him did he? "I mean, Gabriel won't sleep on the floor and it's not fair to make you sleep on the floor so you can sleep in my bed. I can sleep on the floor." Castiel said quickly.

"I can't do that Castiel." Dean said and Castiel could feel himself going red. Why did he have to suggest it to Dean in the first place? Why?

"Dean just take the damn bed." Castiel said sternly trying to stop this conversation from expanding. "If you try to sleep in the same room as Gabriel he will keep you up all night with random questions like if you had a body double in _Train Tracks To Albuquerque_ or if it was really your ass." Castiel added rolling his eyes.

"Seriously?" Dean asked smirking.

"Oh yes, please just sleep in my room. It would save your sanity in the end." Castiel said nodding towards his bedroom.

"As long as you're sure." Dean said shrugging. Castiel gave him a brief smile then turned away from Dean to walk into the bathroom. He could get Dean something to sleep in because the thought of Dean Winchester sleeping in his in just a pair of boxers or even less was not something Castiel should have been thinking about. Castiel was just reaching the bathroom when Dean coughed.

"It wasn't." Dean said and Castiel turned back to look at him with a quizzical look.

"What wasn't what?" Castiel asked.

"It wasn't a body double." Dean said winking at Castiel before he walked into Castiel's bedroom. The _asshole_…

* * *

Dean smiled to himself as he glanced around Castiel's room. The room looked more like a bookstore that happened to have a bed in it than an actual bedroom. The walls were covered in poster versions of book covers ranging from _The Great Gatsby_, _To Kill A Mockingbird _and _Other Voices, Other Rooms_. Nearly all the books in the room looked well read and very dog-eared. There were more photos of Anna and Castiel in here as well as a large photo clearly taken at Castiel's high school graduation. He was standing next to Anna and a middle aged guy that Dean assumed was his father because they looked quite similar. Dean was just glancing at an old and worn looking photo of a smiling woman with what looked like Castiel and Anna as small children when the bedroom door opened. Dean tried to look like he hadn't been snooping and quickly straightened himself up. Castiel gave him an awkward looking smile as he came into the room.

"Um…I thought that you'd want a t-shirt or something to sleep in. They should fit you and they're straight from the laundry so they're clean." Castiel said quickly as he placed a t-shirt and some worn looking sweatpants onto the bed. "Sorry if the room is a bit of a mess…I tend to forget that most people don't live under piles of books."

"It's fine Castiel…it's…well it looks peaceful."

"Yeah…it is until a stack of books falls you in the middle of the night."

"How many times has that happened?"

"More times than I would care to admit." Castiel said and a smile danced across his face for a moment before he quickly looked away from Dean. "I'll leave you to sleep or whatever…night."

"Yeah…see you in the morning Castiel."

"If Gabriel wakes you up in the middle of the night wanting to know anything inane and stupid then just smack him with a book." Castiel said and Dean was sure he wasn't actually joking. Castiel left the room leaving Dean alone. Dean picked up the clothes that Castiel had left him. They were worn looking and on Castiel they would look oversized but when Dean pulled them on they were a perfect fit and very comfortable. Despite the good night out with Anna thoughts of Castiel were beginning to invade Dean's brain. He would say that this was because he was wearing Castiel's clothing but deep down he knew that wasn't really true.

* * *

**Author's Note: Ha and I said I wouldn't write another 8,000 word chapter…what am I even doing with my life? I hope you guys are happy and that this chapter isn't too shitty.**

**The next update _should_ be on Saturday. **


	9. Chapter Nine

**Chapter Nine**

"So Winchester, when are you coming back to New York?" Jo asked as soon as Dean picked up his phone after the third ring. He and Anna had been sat in a small cafe near Anna's apartment and Anna had just left him to retrieve their drinks form the counter when his phone had rung loudly. Dean was relieved when he saw Jo's name on the screen and not Pamela's.

"Why? Are you missing me so much already?" Dean asked. He heard Jo huff loudly down the phone and couldn't resist smirking.

"Huh, you wish." Jo snorted. "I just want to know because then you can be the one to answer constant questions about the endless photos of you and that Anna girl that have been splashed across gossip magazines and nearly every celebrity gossip blog on the internet. I'm being bogged down at work with questions, plus there is a party at my friend Petra's house on Friday night so I need my wingman." Jo explained while Dean glanced around the cafe. It was a small and cluttered looking place and it seemed fitting that apparently both Anna and Castiel spent a lot of time here drinking coffee.

"Since when have I been your wingman?" Dean asked.

"Since eighth grade when I developed boobs and you developed a pout." Jo said bluntly and Dean really didn't have an answer to that. "So when are you coming back?" Jo then asked sounding persistent.

"Probably on Thursday. Pamela left me a message that she wanted to meet me on Friday morning." Dean said as his stomach sank at the thought of having a meeting with Pamela after he'd been ignoring her phone calls since the morning before.

"Do you think it's about that film you're up for?" Jo asked suddenly sounding less mocking than before but that was probably because she knew how much Dean wanted this role. "What do you think Pamela is going to say to you?"

"Honestly? I have no idea Jo." Dean said. "Look, I'm having coffee with Anna right now, can I call you back later?" Dean asked and he heard Jo huff loudly again.

"Fine, you go off and flirt with the 'Win A Date' girl while I just stand here and serve overpriced coffee to the huddling masses of New York." Jo said. "I hope you realise that the internet is full of photos of the pair of you out and about in Chicago…how much do you hate camera phones."

"With a burning passion and you know that, now go back to work." Dean said as Anna came back to their table and placed a coffee in front of him. "I'll talk to you later Jo." Dean added.

"Catch you later Winchester, enjoy your flirting." Jo said before she hung up. Dean placed his phone back into his pocket before he looked across the table at a smiling Anna.

"is everything ok?" Anna asked curiously.

"Yeah, it was just my best friend Jo back in New York. She was wondering when I was going back and she always loves to mock me whenever my face turns up on the internet or in a magazine."

"She sounds…interesting. How long have you two been friends?" Anna asked before she took a sip of her coffee

"Since the dawn of time." Dean said with a chuckle "Well that's how it feels sometimes. We grew up together, she's more like a sister sometimes than a friend actually. An annoying sister but a sister all the same." Dean explained before he found himself glancing around the café again. Like the bar it had that mix of bookish looking students scattered around the place and it seemed as though many of them didn't have a clue who Dean was but every now and then he would notice someone look over at him and then double take. After a few moments he heard the familiar click of a camera phone. Dean truly hated that dickhead that decide people should be able to take a photo whenever and wherever they were. The amount of slightly fuzzy pictures that Jo had sent him, purely because she said his face looked funny in them, drove him insane. The day that she had discovered something call a GIF had been the day Dean's email had exploded with countless attachments from Jo of Dean pulling funny faces on the red carpet. Dean really hated the internet sometimes. Anna noticed Dean's face and gave him a sympathetic smile.

"That must get really annoying after a while huh?" She asked.

"Yeah…yeah it does. It sometimes feels like I can't go anywhere or be myself because people will constantly be taking photos of me and posting them up on the internet." Dean explained.

"I suppose you never really get used to it either do you?" Anna then asked. "I mean…Ruby sent me all these links to articles that are full of photos of you and I together…it's strange to see my face on the internet though I guess that's what you get from being famous right?" Anna added sounding slightly sad for a moment. For those few seconds that he looked at Anna for Dean felt resentful towards his fame because if he was just a normal guy then he could be sat in a café drinking coffee and not have to worry about having countless photos splashed across the internet.

"Yeah…I mean if I wasn't doing this, if I wasn't an actor, then I would be back in Kansas and probably working with Jo's mom Ellen or at the car repair shop that my friend owns but I wouldn't be happy because I actually enjoy acting you know? I enjoy becoming someone completely different for a while and playing out this whole different life…but the fame that comes with it…well it can sometimes get to me."

"God…you're so different for how I expected you to be…you really are." Anna said with a shake of her head. When she did that it reminded Dean of how surprised Castiel had been to find out that Dean wasn't the person he had thought Dean was. Dean wished it didn't remind him of Castiel, whom he hadn't seen all day because Castiel had been in classes since the morning, but it did. No, he was here with Anna and he couldn't think about Castiel at all. "I really expected you to be an egotistical jerk…well not a jerk but certainly more 'Hollywood' than you are."

"That probably comes from being raised in Kansas…and not really having much of an ago. I mean, I'm just a normal guy really."

"Yes because every normal guy has their face all over Times Square."

"Ok, apart from that I'm a normal guy. It's not like I'm one of those actors who goes a bit crazy with their fame and thinks they're the greatest thing in the world. You know, the ones who only ride unicycles everywhere and will only eat organic vegetable grown in their own garden that have been blessed with a moon spell or some bullshit like that."

"Do you actually know people like that?" Anna asked.

"You see some crazy things when going to Los Angeles" Dean said with a slightly chuckle.

"I can imagine…" Anna said between smiling and then sipping on her coffee again. She opened her mouth to say something else when her phone went off with a text message alert. Rolling her eyes slightly she unlocked her phone and read the message. "Gabriel. He's got home alright though he's pissed off that we made him go back home." Anna said. Dean found Castiel and Anna's brother actually pretty amusing though it was clear that they couldn't handle him for more than a few days. Anna had sent Gabriel to the train station to get a train back to Lincoln earlier that day despite Gabriel's protests. "It's a good thing he's gone back home actually, he would have just driven you insane with countless questions about your films."

"Yeah, Castiel said that." Dean said.

"He had a point." Anna said. "Apparently he kept Castiel up half the night with inane babbling. When he left this morning Castiel was holding the biggest thermos of coffee I have ever seen. If he's made it through his lectures today without falling asleep then I will be shocked though they're talking about books and that is what Castiel lives for." Anna said with a casual shrug.

"Yeah, apparently he loves books as much as you art, according to Castiel anyway."

"Probably. I could walk around most of the gallery and art museums here with my eyes closed and still tell you all of the paintings. I spend far too much time in them." Anna said slightly gushing as she spoke.

"It just shows that you're passionate about something, it's nice." Dean said and Anna smiled brightly at him. The way that Anna's face was lit up with her smile made Dean smile himself. She seemed so happy to be here with Dean and yet Dean felt like a bit of a jerk because every now and then he realised that the way Anna's was smiling at him made Dean smile not because she was smiling but because he had made her smile like that…it felt entirely selfish and made Dean feel like a bit of a dickhead.

* * *

On Wednesday night Castiel was hurrying back to the apartment after a late lecture had run on for longer than he thought. He was tired and desperately just wanted to crawl into bed and sleep for about a week despite all the coffee he had drunk during the day to keep himself awake. Hurrying through the lobby he gave a few of his neighbours' curt nods before he started the climb up the stairs towards his apartment. He was walking down the hallway and nearing the door when he heard Anna's laugh and the low rumble of Dean's voice. God, Castiel was very tempted to just turn the other way and go to see Alfie but his bed was seriously calling him. Maybe he could sneak through the apartment unseen and just throw himself into his bed. That plan was shot when he opened the door.

"What's that noise?" Castiel asked when he walked into the apartment and heard a bizarre whirring sound coming from the kitchenette. The sound did not belong to their coffee maker which was really the only appliance he and Anna ever used so Castiel was at a loss as to what it could possibly be.

"That would be the oven..." Dean said from the kitchenette in the same voice you would use when explaining something to a small child and Castiel was very tempted to glare at him. "I've been here for three days and not once have I seen you or Anna eat something that wasn't pre made or something that you just added water to." Dean added as Castiel walked over to the fridge and was shocked to find fresh vegetables, fruit, cheese and meat on the fridge shelves.

"The small weird looking green stuff is called okra apparently...I have no idea what it is either." Castiel heard Anna say from the couch.

"Yeah I think your whole kitchen is in shock from there being fresh goods in it." Dean said as he bobbed his head in time to the music playing from the radio. It took Castiel a moment to place it as Fleetwood Mac, whom his mother used to listen to all the time when he was a very small child. She used to sing Dreams to he and Anna before they to sleep. The thought made Castiel smile for a moment before he noticed Dean watching him. Looking away Castiel glanced over to the oven. Now that he knew Dean was cooking he realised the smell from the oven was baking bread with a hint of garlic.

"I didn't even know the oven still worked after that time I tried to make grilled cheese." Castiel said in surprise and the look on Dean's face just before he burst out laughing was priceless. Castiel wasn't sure what was so funny about him attempting to make grilled cheese but part of him just wanted to say something else Dean would find hilarious just to hear that laugh again and see the wide smile on Dean's face.

"God, no wonder that poor thanksgiving turkey suffered." Dean said between snorts of laughter as he glanced up at Castiel with that damn smile. Castiel was very tempted to be a dick towards Dean just so he would stop smiling but that really wasn't what he wanted at all.

Over the past two days Castiel had managed to keep himself busy enough to not be in the apartment much. He'd spent time in the library writing up his essay and actually attempting to socialise with a few people from his classes. He could tell himself that it was because he needed to both get his essay done and gain some more social skills but he had to admit to himself that it was because he was avoiding Dean Winchester as much as physically possible. Now the smile that Dean gave him was making him grateful that he'd stayed away but it was actually impossible to look away. This was not good at all. Dean was here for Anna, not Castiel so he needed to stop thinking about the damn movie star already before it became painfully obvious that he may or may not be starting to like a guy he thought was a complete and utter moronic asshole up until two days previous. Though Castiel thought that classing it as liking Dean might have been a bit stupid seeing as it less to do with liking Dean and more to do with kissing Dean on the lips and passionately discussing literature.

"So what do we owe the pleasure of your cookery skills?" Castiel asked raising an eyebrow at Dean.

"Well I'm travelling back home tomorrow so I thought I'd make you something that didn't come from a packet" Dean explained as he stirred a large saucepan full of rich looking sauce. Castiel was amazed at the sight of the saucepan actually, he'd been convinced they didn't even own saucepans. "Anna said you didn't have anything against Italian food so I'm going with that." Dean said glancing up at Castiel again with a look like he was trying to seek Castiel's approval.

"Um...no, no I don't have anything against Italian food." Castiel said dumbly as Dean smiled at him again. Dean really needed to stop smiling at him like that because it was swiftly becoming a problem. "You really don't have to cook for us...for Anna..." Castiel said quickly correcting himself because it was obvious that Dean was only doing this for Anna.

"God, you're eating something that isn't Ramen noodles for the first time in days, stop being silly." Anna said coming up next to Castiel and nudging him in the side with her elbow. Dean smiled at him yet again as he opened the oven and pulled out a try of garlic bread that smelt _amazing_.

"I have work that I really need to do though...and I'm pretty tired from my day in lectures." Castiel said trying to think of any excuse not to sit with Dean and Anna.

"Castiel will you just sit and eat with us? It's nice to have people that actually appreciate my cooking. Jo always complains whenever I try to cook her things. I think she's convinced I'm secretly trying to poison her." Dean said rolling his eyes at Castiel before he moved over to grab the only plates that had survived the post-Ryan voicemail plate smashing. Dean quickly served up their food and the three of them made their way to the coffee table where Castiel and Anna normally ate.

"So where did you learn to cook?" Anna was asking Dean while she sat down on the floor next to Castiel.

"In Italy actually." Dean explained while he placed a plate of fresh garlic bread onto the table. Seriously that garlic bread looked, and smelt, really good. "I was there shooting a film-"

"The remake of Roman Holiday?" Anna asked because she was that much of a Dean Winchester fan. Castiel resisted groaning at the memory of that film which he had been forced to watch at the cinema three times despite his constant protests.

"Yeah, well while I was there I had a few lessons with this great chef and he taught he an awful lot about cooking" Dean explained as he grinned at Anna. Castiel took this moment to take a bite out of his food and _damn_, it was good.

"Holy shit..." He muttered and when he looked across the table at Dean he saw a huge and proud looking smile on his face.

"Good?" Dean asked.

"Can you stay forever and just cook for us?" Castiel asked more to do with the food related orgasm he was having than anything else...well he hoped he could pass it of as that either way. "Um...yeah it's good..." Castiel then muttered looking away from Dean's proud smile.

"My God I think Hell just froze over, my brother was nice to you." Anna said to Dean with a chuckle.

"I think it can happen when he puts his mind to it." Dean then said also chuckling. No, it was more like when Castiel let his guide down and forgot that he was supposed to actively dislike Dean Winchester because it was easier than anything else. Castiel returned to eating his food and was determined to not look at Dean or Anna and swiftly settled on looking down at his food. He really did have to admit that Dean was an amazing cook and going back to eating Ramen noodles was going to be depressing no matter how much he loved Ramen noodles.

"Where are you going?" Anna asked looking up at Castiel with furrowed brows and a quizzical look.

"I have work that I really need to do Anna." Castiel said.

"I made pie for dessert" Dean called but Castiel shrugged his shoulders. He really needed to get out of this room as soon as possible.

"Castiel-" Anna started to say but Castiel just shrugged his shoulders again and walked into his room as quickly as he could. Things were fine until he remembered that he had let Dean sleep in his bed the night before. Fuck…why couldn't he have just made Dean sleep on the floor? Castiel would be glad when Dean just went back to New York because then Castiel go hopefully go back to just think he was an asshole and a useless actor. Having Dean here was making Castiel forget that he was supposed to hate the guy and yet he couldn't stop thinking about Dean, the Dean he'd gotten to know over the past days thankfully and not the Dean Winchester whose face was pretty much everywhere.

* * *

By the next morning Castiel had finished all the work that was due for the next two weeks, rearranged his bookshelves alphabetically by author and also sorted out his socks which hadn't done since…well he'd never actually sorted his socks so that was first. I guess that's what happens when you're determined to ignore your twin sister and the millionaire movie star she may or may not be dating/seeing.

As he didn't have any lectures or classes that morning Castiel was sat on his checking through his emails though most of them were either from Gabriel who was complaining about several mindless things or they were updates from literary blogs that he followed. He was clicking onto a link when there was a knock on his bedroom door. He hoped it was Anna over Dean because even if Anna questioned him about why he had gone to bed so early last night that would be better than talking to Dean.

"Cas?" Castiel heard someone call. "Castiel?" He looked up from his laptop and watched as Dean walked into his room holding his car keys. "Hey man, I just wanted to say goodbye. Thanks for letting me crash here and everything. It was good meeting you." Dean said hovering in the doorway looking awkward. Castiel did this nervous little twitch that made him feel like a complete moron as he moved his laptop away from him. He rose off his bed cumbersomely and ran his palms against his jeans as he felt them begin to sweat. God, he seriously needed some help.

"Yeah…it was good meeting you Dean." Castiel said reaching out to shake Dean's hand because it seemed like the politest thing to do. Castiel would have preferred to insult Dean because then it would make it easier for Dean to hate him but it really didn't seem like the right time for that at all.

"Wow, you didn't call me 'Hollywood Ken'." Dean said with a playful smile.

"Yeah, I'm putting my mind to it." Castiel said sarcastically and he really wished that Dean would stop smiling at him because it was making it harder to mock Dean. Dean chuckled and instead of shaking Castiel's hand he pulled him into a quick one armed hug. Dean was solid, warm and had the type of body that you just wanted to hug. It was not helpful for the situation at all.

"It was really good meeting you Cas…Castiel." Dean said when he pulled away. Castiel was resolute in his decision not to look at Dean but he couldn't help it. God, he never realised that Dean had freckles dusted across his face. Yes, none of this was helpful to the situation.

"You too Hollywood Ken." Castiel said giving Dean a sardonic smile and he was sure he saw Dean's own smile waved for a moment and a completely different look replace it but then the smile was back and Dean was nodding his head. He looked at Castiel for one more time before turning away and walking out of the room leaving Castiel alone. "Fuck" Castiel muttered under his breath before throwing himself back onto his bed, hitting his bed on his laptop in the process. "Ow.." he groaned hating himself for that moment in time..

* * *

Dean banged his head against his steering wheel and let out a low groan of annoyance that was more at himself than anyone else. He'd literally just said goodbye to Anna and yet all he was thinking about was the fact that he'd hugged Castiel. He'd hugged him. Of all the boneheaded moves he could have done hugging Castiel was near the top of the list. He'd promised Anna that he would speak to her as soon as he could and yet now all he could think about was how for a brief moment he thought that Castiel had hugged him back. Fuck, Dean really was in trouble and he had no one to blame but himself…and maybe Castiel…

Ok this drive back to New York was going to a long one that could only be helped with music so loud that it forced Dean not to think. Looking through his collection of CD Dean pulled out one at random and shoved the disk into the CD in the dashboard. The sounds of ACDC filled the car and Dean settled himself back in his seat and tired as hard as he could to not think about either Anna or Castiel…especially Castiel.

By the time Dean got back to New York he was tired, stiff from not really stopping and there was a pretty bad ringing in his ears from the constantly high volume of his music. On the plus side he hadn't thought about Anna or Castiel…much.

He was happy to reach his building though, sleeping in his own bed and waking up to the New York skyline was something had missed over the past several days.

"Have you just stayed here the entire time that I was away?" Dean asked throwing his jacket down onto the nearest chair and waltzing over to where Jo was sat.

"I was doing my duty as a good friend by watering your plants and getting your mail." Jo said smiling happily.

"I don't have any plants in this apartment." Dean pointed out.

"Ok I snooping through your mail, eating your food and watching your flashy TV, does that make you feel better?" Jo asked rolling her eyes heavily.

"Not really." Dean said.

"Well tough because that's what I've done. Now sit down so you can tell me all about your lovely jaunt to the windy city…oh and you need more cereal." Jo said. Dean sighed and sat down next to Jo. She handed him a bottle of beer and was soon badgering Dean over what had happened in Chicago. Dean told her everything apart from the very obvious fact that he might have been developing feelings of…something for Anna's overly sarcastic brother that Dean was pretty sure still didn't actually like him as he'd gone out of his way to avoid Dean over the past few days. Jo was actually a good listener and nodded at all the right parts of Dean's story and didn't make half as many jokes as Dean thought she would make.

"Oh apparently you should call Sam." Jo said after an hour of Dean telling her about his trip to Chicago.

"And how would know that?"

"Because he told me that you should call him." Jo said like it was the most obvious thing in the world. Dean refrained from rolling his eyes at Jo.

"He couldn't have just called me?" Dean asked.

"He did but you just have been driving because you didn't pick up your phone." Jo said shrugging. Dean sighed and went to look at his phone. Sure enough there were several missed calls all from Sam and three text message from Pamela. The messages from Pamela could wait but speaking to his brother was something Dean needed to do right now. Dean dialled Sam's number and walked into his bedroom so he didn't have to contend with the noise from the TV.

"Hey Dean!" Sam said when he picked up the phone. "What's up?"

"Well according to our lovely Jo you wanted to talk to me." Dean said.

"Oh yeah! So I see how it is Dean, you'll use me as a cover so run off to Chicago but you won't come to California to see me?" Sam said but Dean could hear the smile in his voice.

"Shut up bitch, I came to California a few months ago to see you." Dean pointed out. "Besides it was the only lie Pamela would have believed." He added.

"Until there were photos of you in Chicago posted online." Sam pointed out sounding smug.

"How do you know that?" Dean asked.

"E! News web alerts, Jess has them on her laptop plus Jo told me." Sam explained like it was obvious. Stupid E! News... "Who was the guy you were with?" Sam then asked.

"Anna's brother Castiel, we went for a drink." Dean said trying to sound as nonchalant as possible.

"Meeting the brother already?" Sam asked chuckling.

"They live together, they're both at University of Chicago. Unlike some people Anna doesn't hide siblings away." Dean said trying to steer the conversation back towards Sam so that his brother would question him about Castiel because he was not in the mood to talk Sam about Castiel at the moment.

"Hey it's pretty impossible to hide you when your face is everywhere and I'm not hiding you, if anything I'm hiding Jess." Sam said. "What's her brother like?" Sam then asked and Dean tried not to groan.

"Cas...Castiel? He..." Dean started to say but he stopped himself for a moment because telling Sam all about Castiel would confuse the lines more than already. "He's ok..." Dean said after a moment. "He's sarcastic and really loves his books..."

"But you get on with him right?" Sam asked. Dean shrugged until he realised that Sam couldn't see him. He thought he got on with Castiel alright even if Castiel was sometimes off with him or overly sarcastic about something but there was no way that Castiel liked him in the same way as Dean was beginning to like Castiel, if anything Castiel tolerated Dean because he knew that his sister liked Dean. "Dean?" Sam asked and Dean realised that he'd been silent for several moments.

"Oh yeah...yeah we get on alright." Dean said quickly.

"So if you're hanging out with Anna's brother then that must mean that you're serious about taking things with this Anna girl further right?" Sam said.

"I...I don't know."

"What does that mean?"

"Being with Anna would be a lot easier." Dean explained hoping that made sense.

"Easier than what?" Sam asked.

"Than nothing, it would just be easier ok?" Dean said. He hated not being able to tell Sam the whole truth about what was going on with him but it just made things easier at the time.

"Do you really like her?"

"I like her and like I said, it would be easier."

"I still don't understand what the hell you mean by that but that really doesn't sound like a reason behind being with someone."

"Well them why are you with Jess?" Dean asked.

"Because I've never another girl like I've loved her before. I can't see myself with any other person on my life and she makes me feel line the luckiest person in the world to have her in my life." Sam said seriously and Dean's stomach sank because even though he liked Anna he doubted he would ever like her in that way. Sam was with Jess because he truly loved her, it was clear from his voice, but Dean had to admit that he wanted to be with Anna for a lot of his own selfish reasons. "Have you ever met someone that you think could make you a better person but you're not around them for just that reason, you're around them because you can't picture yourself not seeing them?" Sam asked and Dean could of kicked himself when he thought not of Anna but of Castiel. Fuck...he really was in trouble.

* * *

**Author's Note:**

**Yes this is kind of a filler chapter but that's only because the next chapter is going to be pretty long and, hopefully, exciting.**

**Oh, I had a few people on tumblr ask me how many chapters there are going to be and I can now say that there is going to be thirteen chapters so the whole fix should be finished within the next two weeks.**


	10. Chapter Ten

**Chapter Ten**

Pamela's office felt stuffy and claustrophobic like always. Dean had not gotten enough sleep the night before and he certainly hadn't drunk enough coffee to be fully conscious for this meeting. Pamela's look of fury was also not helping matters. If she didn't make him do some embarrassing commercial as a form of payback for Dean lying to her then he was going to be very shocked.

Pamela was sat at her desk typing frantically about something that Dean didn't bother asking about because Pamela seemed like she was in the mood to yell at him. Dean wished that he'd gone for coffee before the meeting; he was finding it very difficult to keep awake.

"Pam-"

"One minute Dean." Pamela said raising a hand up to silence Dean.

"Sorry" he muttered sitting back in his seat feeling very much like a small child. Pamela had been pissed that Dean had gone to Chicago but the countless photos of him and Anna splashed across every gossip website possible had slightly softened her because of the positive light it had cast on Dean.

"Well…well Dean I've called you into this meeting because…well…the _Diversion _people have finally stopped breathing." Pamela said after several minutes of typing. She looked away from her screen and her eyes met Dean's.

"Figuratively or factually?" Dean asked and Pamela's pursed lips told him that he should stop making anymore jokes before she stabbed him in the face with a pencil. It was highly likely that she might do that as well.

"They rang me while you were swanning around Chicago and I'm sorry to say but they have decided to go in a different direction with the film. Apparently they want a more mature feel to the film and have decided that the character of Marcus should be a middle aged father, not a twenty-something year old." Pamela explained.

"So that means…what exactly?" Dean asked narrowing his eyes.

"It means that you didn't get the part Dean, I'm sorry because I know how passionate you were about this film." Pamela said actually sounding very consoling for once. "I'm still talking to the producers of the independent film though and there are several other projects in the pipeline so try not to be so upset."

"Yeah…I understand Pamela…" Dean said even though in that moment he felt like complete shit. He only stayed in Pamela's office for several more minutes while she carried on talking, thought Dean wasn't listening at all if he was honest, until she demised him from her office. Dean was barely out of the building before he was ringing Jo to complain.

"Damn, I know how much you wanted the part so I'm really sorry." Jo said once Dean had stopped ranting to her. "I finish work at six so how about we go to that fancy bakery downtown and buy an apple pie the size of your head? After that we can pray that the film bombs at the box office." she asked and it was as if she had read Dean's mind.

"And this, Joanna Beth, is why I love you sometimes." Dean said.

* * *

_One Month Later_

After never leaving Illinois before nearly two months ago Castiel was now very surprised to find himself in New York for a second time. The city was unlike anywhere he'd ever been to in his life before and just knowing that he was there actually gave him a real rush. He was surrounded by so much culture and the air actually smelt like endless possibilities…as well as pretzels, traffic fumes and dog pee but he was the ignoring them for the more desirable former. He was in New York and he was determined to enjoy himself.

Not that he was there for a fun excursion at all. If anything he was here to work as he was in New York because of a research trip arranged by his university so he hadn't had any time to himself yet apart from now and that was only because he'd purposely left his fellow students so he come aimlessly wander around the city while trying not to feel like an obnoxious tourist. His bank balance wouldn't let him buy his weight in books from the Strand again so he settled on walking around and trying not to make it obvious that he was taking photos of street art or architecture that he knew Anna would get a kick out of. Ok and he really wanted to try one of the famous pretzels but that wasn't _too_ touristy…he hoped.

"Cas? Castiel?" Someone called out from behind Castiel just as he'd taken a photo some stone gargoyles that Anna would have loved. Glancing around the sidewalk Castiel's chest constricted when he saw none other than Dean Winchester standing outside a Starbucks holding a large paper cup. Dean slowly removed the sunglasses covering his eyes and looked at Castiel as if he had just fallen out of the sky. Castiel knew his face was flushed and yet for the life of him he was not sure why. Yes he might have thought about Dean once or twice since Dean had come to Chicago but that had been because of…well Castiel wasn't really sure why he'd been thinking about Dean and now seeing him in the flesh was making Castiel wonder if he had been thinking about Dean for Anna's sake or his own. Ok it was for his own sake he had to admit that but Dean didn't need to know that…ever. He also didn't have to admit that by 'once or twice' he meant 'once or twice a day'.

Anna had been keeping in contact with Dean via email and text messages but what they talked about Castiel did not know because he was determined not to ask and whenever Ruby brought it up in conversation he would swiftly tune about whatever they were saying. He did not want to know anything about what was going on between Anna and Dean; it was just easier that way.

"Oh…hello." Castiel said instantly hating how stuttering he sounded because Castiel never stuttered. Ever. He was acerbic to the point of annoyance but he never stuttered. He left that to either Anna or Gabriel.

"Hey man, it's good to see you." Dean said sounding quite genuine actually which was surprising considering Castiel was normally a dickhead towards him and Castiel wasn't remotely afraid to admit that. Heck, Dean was a movie star after all; his ego could do with being taken down a few pegs and if Castiel was cynical and contemptuous towards Dean then hopefully he would never mistake anything between for friendship or…more. "What are you doing here in New York?" Dean asked.

"Oh…I'm here with the University for a few days on a research trip. Today is actually our last day here." Castiel explained. He had enjoyed his time in New York but he was very grateful that he had been able to take some time out for himself and wasn't with any of the others or he would have to explain an awful lot about why Dean Winchester of all people was being nice to Castiel. Also he could walk around New York with his headphones in and not have to worry about making conversation with anyone…until now when Dean was talking to him of course.

"Oh…" Dean said and Castiel wondered if that was disappointment that Castiel was hearing in Dean's voice. It couldn't be because there was no reason for Dean to be disappointed right? "I bet you've really hit the city hard though, you know being here with other students and all." Dean then said chuckling lightly.

"Not really actually. We were here on a research trip so we haven't actually gone out anywhere." Castiel explained. "We've mainly stayed in our rooms when we haven't been working."

"Shit, you're joking right?" Dean asked and Castiel shook his head. "Jesus dude, you're in New York. How can you not go out?"

"We're all literary students here on a research trip that has mainly included us walking around countless libraries and the odd museum so it's been very tiring." Castiel explained.

"I bet you loved it though" Dean said with a slight chuckle if he knew just how much of a kick Castiel had gotten from being around all of those books. "Listen…if you're not doing anything tonight then why don't you hit the city with me? I still owe you for crashing at yours the other week anyway. I'm going out with my friend Jo and she'd probably love you." Dean said sounding…well nervous. It was like he was worried that Castiel might say no or that he had plans with the students from his university. Castiel should have said no, he should have told Dean that he couldn't stay in New York for an extra night because he had to work but he didn't.

Despite his furious determination to not think about Dean he couldn't actually think of anything else he would rather do than spend time in New York with Dean. Castiel had actually had fun the last time he'd gone to a bar with Dean and their conversation had been interesting so why shouldn't he go out with Dean for the night? So, instead of saying that he couldn't stay in New York he said:

"That sounds good actually. The others were planning on just grabbing some food then getting the plane back to Chicago later tonight but your plan sounds better." Castiel said and he wasn't afraid to admit that it was true.

"Well you can crash at mine tonight, I like I said I owe you after I crashed at yours." Dean said. Ok Castiel really should have refused that because staying at Dean's apartment would only create more problems but his mind was becoming too clouded and instead of disagreeing with Dean he just nodded and then swiftly hated himself for the pang that shot through his chest when Dean smiled broadly at him. "How about I give you my address? You can come round later…um…my brother is staying with me until tomorrow so you'll meet him as well..."

"The future lawyer? So he doesn't raise people's blood pressure as soon as he walks through the door like my brother then?" Castiel asked and Dean shook his head while chuckling.

"No, no offence to your brother but Sammy is nowhere near as irritating."

"Dean, I can safely say that 'irritating' is the nicest possible way to describe Gabriel." Castiel said. Dean looked like he was about to say something but his phone beeped loudly. He glanced at the screen and groaned slightly. "Is everything ok?"

"It's my agent Pamela, like always. I'm never too far away from the woman who tortures me." Dean muttered pocketing his phone. "My presence is required apparently…I'll see you later then?" Dean asked giving Castiel an inquiring look.

"Yeah…" Castiel said just entirely sure how he'd gone from taking photos of street art to talking to Dean Winchester and accepting his invitation to go around New York with him…with alcohol. The world was a very funny place at times.

* * *

Castiel walked back to the hotel he and his fellow students were staying at in a slight daze thanks to his encounter with Dean and he was still incredibly confused as to why Dean had invited him out for the evening. Was Dean just doing it as a favour to Anna? The thought that Dean was only being nice to him because of Anna made his stomach physically drop in an incredibly painful way.

"Are you coming to get food with us Castiel?" One of the students, a girl called Hester, from his literature class asked Castiel when he caught up with the group who were all sat in the hotel's small bar drinking coffees and glasses of soda. "We're going to take our stuff with us then go to the airport early." Hester added. "We don't want to miss our flight back or anything like that."

"Um…actually I ran into a friend of mine who lives here in New York. I hope you all don't mind but I said I would go out him tonight so we could catch up." Castiel lied, well it was a sort of lie he guessed. He could catch up with anything that had been going on with Dean though he couldn't really call them friends.

"Really? I didn't know that you had friends here in New York. Won't you miss the flight back to Chicago?" Hester asked sounding slightly annoyed at Castiel's plans even though she had reason to be.

"Yes, I can get the train back after I've caught up with my friend though." Castiel said with a shrug. He was not going to mention that he'd be staying in New York for an extra night because Hester would just ask him more questions.

"Oh ok then, I can take your research back with me and drop it off with Anna if you want me to." Hester said because even if Hester was annoyed at you she would still go out of the way to do something for you. It was actually very sweet, it was just a shame that Hester could get very shrill at times and she had far too many opinions that she felt everyone needed to know.

"That's really nice of you Hester, thank you." Castiel said trying very hard not to sound derisive as he was actually being sincere for once. The way Hester frowned for a moment confirmed Castiel's speculation that he did sound slightly sarcastic but if he was being honest Castiel was part caring.

"Yes…well…enjoy your night then Castiel." Hester said sniffing slightly as she turned away from Castiel to talk the rest of the group. Castiel gave Hester a shrug of his shoulders before he went back upstairs to his room to shower and get changed.

* * *

Dean's apartment building was in an upscale part of New York which really did not surprise Castiel at all. It was a large building and it even had a bloody doorman. A rude doorman at that who looked Castiel up and down several times before he let him into the building after Castiel told him that he was here to see Dean. God, he really should have said no to Dean's request but instead he was now walking through a fancy looking lobby to an even fancier looking elevator. Jesus…

Dean was the one who opened the door and Castiel couldn't help but smile when he saw Dean. Castiel hated, really hated, how his chest constricted when Dean smiled at him because none of this was going to end well and he knew that, he really _knew_ that. He should just make up an excuse, turn and run as fast as could but then he looked at Dean's smile again and Castiel knew there was no way he was going to be heading back to Chicago that evening at all.

"Hey come on in." Dean said nodding inside the apartment. Castiel followed him inside to a large and very open looking apartment. Castiel looked around with an impressed look.

"It's…nice."

"Well it's not university student nice but it's decent." Dean said grinning over at Castiel. Castiel stopped for a moment before returning Dean's grin. A cough behind Castiel caused Dean's smile to falter slightly and Castiel looked behind him to see a small blonde walking from the open kitchen with a sneer across her face.

"Well, well, well who do we have here Winchester?" she asked.

"Have you just permanently moved in here or something? I hate to remind you that you have your own apartment with post that needs reading and food probably growing mould on it." Dean said though the way his said it was with love.

"Don't be such a downer Winchester. Your apartment is nicer plus you have _HBO_. I need my _Game of Thrones_ fix." The blonde said. "And, I think I asked you a question and that question was 'who do we have here?'" the blonde added.

"This is Castiel, Anna's brother." Dean said. There was movement from the couch as someone Castiel hadn't noticed before stood up with a broad smile on his face.

"You're Anna's brother? Cool, Dean's told me a bit about you. It's really nice to meet you."

"This is my brother Sam." Dean said nodding towards the tallest person Castiel had ever met. Castiel wasn't short by any means but standing in front of Dean's brother made Castiel feel like one of those overly perky short people from _The Wizard of Oz_. Dean's brother smiled at Castiel like a small child would smile at a puppy and Castiel couldn't help but smile back despite feeling awkward standing here in Dean's large apartment. "And this is my oldest and best friend, Jo." Dean said nodding towards the short blonde that was stood near Sam. She had a pretty face and bright smile that was the kind of smile you couldn't help but smile at as well. Normally meeting new people freaked Castiel out because most people thought he was an awkward and sarcastic jerk. Meeting Jo and Sam actually didn't make Castiel feel as nervous as he thought he would be which he thought was a very good thing.

"Actually I'm his only friend; no one else really likes him minus Sam but Sam has to like him because they're related." Jo said with a sly grin directed towards Castiel. "So you're Castiel." The small blonde said looking Castiel up and down like he was a prize cow at the county fair. He had to admit it was starting to make him feel slightly uncomfortable even if Jo wasn't too intimidating yet he continued to look back at her, he wasn't going to be the one to look away. "Well I have heard absolutely nothing about you from Dean so that means one of two things."

"Oh? And what would those two things be Joanna Beth?" Dean asked raising an eyebrow.

"Don't start middle naming me Winchester." Jo said glaring at Dean for a moment before turning her attention back on Castiel. "The first thing could be that you're so angelic that Dean has been hiding you for fear of you being corrupted by myself _or_ it could be the second option which is that you're the exact opposite and highly devious therefore Dean is hiding you for fear of _you _corrupting him and me." Jo said.

"I'm from Illinois, I'm hardly that Machiavellian." Castiel said refraining from smirking when he saw Dean give Jo a face that was clearly that of a man of was done with the conversation. Jo spotted this look and looked very pleased with herself for getting a rise out of Dean while Sam snorted from where he was stood.

"Doesn't Illinois have a really high murder rate?" Jo then asked Castiel.

"Yes but I can't be blamed for that unless I murdered anyone in the area and as far as I can recall I have not committed any homicides yet." Castiel said giving Jo a smile that she swiftly returned.

"Well you would hardly admit to it." Jo said. At this point Castiel thought that Dean was going to hit Jo over the head with the nearest bottle. "Oh stop pouting at me like that Winchester, I like this one." Jo said smiling over at Castiel. "Though my entire opinion of you will rest on your answer of the following question, what are your opinions on tequila shots?"

"Positive?" Castiel said somewhat dubiously because he'd only drunk tequila twice before and both of those times had ended with him passed on in his bathroom but admitting that in front of Dean, Jo and Sam was not something he was up to doing. Especially as Jo seemed like one of those achingly cool people who probably worked at a coffee house and only listened to vinyl records.

"Oh this one is a keeper Winchester." Jo said clapping her hands happily.

* * *

In the end it was Jo's decision to go to a club. Castiel would have preferred somewhere quieter but at least this way he wasn't remotely tempted to start a conversation with Dean. The club wasn't far from Dean's apartment so they walked there. Castiel had questioned how Sam could have gotten into the club seeing as he was still a minor but Jo had laughed that away by telling Castiel that Sam had owned a fake ID since he was seventeen.

Within moments of entering the club Jo had lumped Sam with drink duty while she dragged Dean off with her towards the dance. Castiel watched with a smirk as Dean flashed both him and Sam a terrified look. Castiel followed a smirking Sam to the bar to get drinks.

"So you're studying at Stanford right? How is that?" Castiel asked Sam as he leant against the bar. Talking to Sam Winchester seemed to be a safer option than dancing over on the dance floor with Jo and Dean. Plus Sam seemed like an interesting person and was clearly smart as he was studying to become a lawyer, Castiel didn't mind at all that he was talking to Sam really.

"Stanford? It's great. I mean the work is hard but I love it...I've wanted to become a lawyer since I was younger so it's a great feeling knowing that I'm working towards that. You're at the University of Chicago aren't you?"

"Yes, I'm studying English Literature." Castiel explained in between sips of his beer. Over on the dance floor Jo was laughing loudly even over the music as Dean twirled her around the in circles. A slow and sincere smile crept across Castiel's face as he watched Dean; he looked so relaxed and free and so unlike the slightly cagey person Dean seemed to be. It took a moment for Castiel to realise that Sam was watching him watch Dean and his cheeks flushed. Sipping his beer he tried to look nonchalant but he knew that probably didn't work.

"He's not the pig headed or arrogant ass that people think he is, though I do think that he brings it on himself by being so standoffish towards a lot of people." Sam said looking over at Dean before turning back to Castiel with a warm smile. "He told me a lot about you, apparently he was really concerned that you thought he was a moronic dickhead when he first got to Chicago to see your sister." Sam added.

"I really can't imagine why." Castiel said though he was slightly pleased that Dean sought Castiel's approval though that was probably because Dean was seeing Anna.

"Really?" Sam asked raising an eyebrow before taking a sip of his beer. Castiel was about say that he really had no idea why Dean would want his approval apart from because of Anna but he was interrupted by Jo dancing up to him and taking him by the hand.

"Come on Castiel Milton, you can't come all the way to New York and not dance your skinny ass off." Jo said into Castiel's ear with a huge grin on her face. She dragged Castiel over to where she had been dancing with Dean and returned to dancing wildly. Castiel hated dancing because he never knew what to do with his feet and he was always conscious of looking like a fool but he tried his best and everything's was going alright, he hasn't fallen over or hit anyone in the face, until there was surge of people and Castiel found himself pressed up close to Dean. If he wanted to he could just reach up slightly and they would be kissing. He wanted to. He wanted to kiss Dean but they were in the middle of a packed bar surrounded by people, Dean was seeing Castiel's sister and most importantly Dean was straight so kissing him would not be a good idea at all.

Still, the heat between them was making Castiel's skin burn and as he felt Dean's hip move against his own he felt a rush of electricity run through his veins. Turning his head slightly he noticed Jo watching him and Dean with a knowing look on her face that made it clear that she knew what Castiel was thinking. This was not good. He had to get away from Dean and back to standing by the bar where there was no chance of his hips touching Dean's.

"I'm going to get another drink!" Castiel said loudly over the music as he pushed his way back to the bar where Sam was talking to a tall girl who, by the sound of the conversation studied Law at Yale. Castiel ordered another beer and drained the bottle in one go.

"Whoa, you ok Cas?" Sam asked him and Castiel nodded his head quickly.

"Yeah, I just needed another drink." Castiel said shrugging his shoulders. Sam raises an eyebrow again. "I'm fine" Castiel tried to say sounding more convincing than he had before yet Sam's eyebrow stayed raised for several more seconds before he shrugged and drank his own beer.

* * *

Five beers later and things started to get slightly blurred around the edges Castiel found himself dancing with Jo several more times and at one point he could have sworn that he and Dean had a conversation but what it was about Castiel really could not tell.

"We're heading back to the apartment!" Jo cried into Castiel's ear over the music. She must have drunk more than Castiel thought because she was starting to stumble slightly as she walked. "Come Milton, move that cute ass of yours!" Castiel heard Jo yell.

"Do we need to get a taxi back?" Castiel asked Sam nodding over at Jo. Sam shook his head as they followed Jo and Dean out the club.

"No, Jo will find a way to get back to Dean's without having to actually do anything." Sam explained wearily. "She always does"

"Sam!" Jo cried as if on cue as she turned round and grinned brightly at Sam. Sam took this all in his stride and just gave Jo a pleasant smile, the same smile you would give a young child.

"Yes Joanna Beth?" Sam said sighing slightly. Clearly Dean knew what was about to happen because he'd begun to snigger.

"My feet hurt." Jo whined. Sam sighed again yet carried on smiling pleasantly at Jo while Dean walked over to Castiel with a smile of his own. Castiel glanced over at Dean and returned the smile though he raised his eyebrows towards Jo questioningly.

"All aboard the moose express!" Jo said happily as Sam nodded reluctantly and let Jo leapt onto his back, piggy-back style. "Mush, mush!" Jo said smirking happily as Sam began to walk down the road with her still on his back.

"How often does that happen?" Castiel asked Dean.

"More often than Sam would care to admit." Dean said between his laughter. The pair settled into a silence that wasn't remotely awkward, if anything it felt comfortable and safe, as they walked side by side. In front them Jo was laughing huskily as Sam continued to carry her road the road and Castiel knew there and then that he had certainly made the right choice by staying here with Dean even if he was more conflicted than before. Not to mention incredibly tired. He was actually very surprised that he was still able to move one foot in front of the other as he'd been awake for nearly twenty four hours. As they neared the street Dean lived on Jo became quieter until Sam confirmed that she had fallen asleep.

"Whatever you don't wake her. We may be able to get at least eight hours of silent Jo if we're lucky." Dean said to Sam as he rummaged around in his pocket for the keys to his apartment building.

* * *

Having Castiel in his apartment was a strange experience. Yes Castiel had been in it only a few hours before but now it felt different in a way though Dean couldn't place his finger on what had really changed. He watched as Castiel helped Sam place Jo on the couch and once Jo was safely lying down Castiel even cleared away the glasses and few stray bottles off of Dean's coffee table. That shouldn't have made Dean smile at all but it did.

After carrying Jo several blocks back from the club Sam yawned loudly and announced that he was going to sleep. He gave Castiel a clap on the back and a very earnest sounding 'It was great to meet you' before he gave Dean a knowing look. There was too much written in that look for Dean's liking but he refrained from saying anything in front of Castiel.

"Night jerk." Sam said grinning over at Dean.

"Hope the bed bugs bite your Sasquatch ass you bitch." Dean said. Sam flipped him off as he walked into his room leaving Dean and Castiel alone in the room, well apart from a dead-to-the-world Jo. "Um…you can have my bed, after all you put up with sleeping on the floor the other week."

"This isn't a competition you know." Castiel said as he yawned slightly.

"I know…it's the least I can do though." Dean said beginning to feel very nervous. What the fuck was wrong with him? "My room…um…it's through here…down the hall." Dean said nodding towards a hallway. Castiel followed Dean into his room and Dean had to admit that his was starting to wander. He really shouldn't have been thinking about this at all seeing as Castiel was stood right next to him.

"I've…I've had a good n-n-n-night." Castiel said with his final word catching on a yawn. "Sorry." He muttered grinning at Dean. "Yeah…it was a good night. Thanks for inviting me out tonight." Castiel then said.

"It's fine." Dean said feeling so awkward and ever so slightly drunk. "There…are t-shirts and stuff you can wear but it might be slightly big on you."

"It's fine." Castiel said shrugging between another yawn. He pulled off the jeans he was wearing, followed by his shirt as well until he was left stretching in just a pair of boxer and a thin t-shirt. Dean tried to look anywhere else but at Castiel though it seemed impossible. He looked so rumpled and tired yet still…still like Castiel. "God…if I hadn't of come out with you I would be back in Chicago now..."

"Did you make the right choice by staying here?" Dean asked. Castiel looked over at him with those fucking blue eyes before he flopped onto Dean's bed.

"Of course I did." Castiel said, his voice ringing with truth.

"Um…good." Dean said scratching the back of his neck nervously as he glanced around the room so he wouldn't be tempted to look at Castiel in just boxers and a t-shirt. He heard Castiel move on the bed but didn't look over to him until Castiel chuckled slightly. Dena looked back and saw Castiel looking at a book on the bedside table. It was _The Great Gatsby_, a book that Castiel had spoken about when they had properly met. He'd said it was one of his favourites. "Yeah…well you said that you loved it and I was curious." Dean said with a slight shrug. Castiel flicked through the book quickly until he landed on a page. "What are you doing?"

"Reading you my favourite quote." Castiel said. Without thinking Dean found himself moving closer towards the bed. The next thing he knew he was sat next to Castiel and watching him quietly read out a passage, his voice clear and low even if slightly tired sounding. "_And so with the sunshine and the great bursts of leaves growing on the trees, just as things grow in fast movies, I had that familiar conviction that life was beginning over again with the summer._" Castiel said in a low voice full of emotion but it was Castiel's lips that caught the most of Dean's attention.

Castiel had lips that were actually screaming to be kissed and it was driving Dean up the fucking wall. Seriously the guy's mouth was almost pornographic to look at and all night they had been teasing Dean with smiles, laughter and exciting conversation.

Those lips were so close it would only take Dean mere centimetres to be kissing Castiel and relieving all the tension he'd been feeling towards him for far too long already; he was seriously beginning to envision it. If Castiel said anything or rebuffed him then Dean could blame it all on the mass abundant of alcohol he'd consumed that evening then they could laugh off it the morning.

"Cas…" Dean said as Castiel placed the book back onto the bedside table. Castiel looked over at him with a tired looking smile.

"No one's ever given me a nickname before…I like it." Castiel mumbled sleepily as he smiled slowly. Without saying anything else he flopped onto Dean's pillow and looked up at Dean, still smiling.

"Cas…" Dean tried to say again but he knew his words wouldn't make the right about amount of sense. Actions would be louder and stronger.

Reaching out gingerly Dean placed his hand on Castiel's stomach feeling the heat of his skin through the thin t-shirt he was wearing. Castiel slowly turned his head and looked at Dean with those damn eyes that were like a punch to the stomach. Cas then smiled so broadly that it nearly killed Dean. Fuck it, Dean thought as his eyes fell to Cas' lips. They were so full and chapped; Dean could imagine chewing on the lower lip before slowly slipping his tongue into Cas' mouth and kissing him fiercely. Moving his hand slowly towards Cas' waist Dean leaned slightly closer and breathed out slightly.

"Dean..." Cas said in a low gravelly voice that made Dean stop. His hand was firm on Cas' solid but slender body and the way Cas was looking at him should have been made illegal. Dean was so far gone by now that he didn't even care about how tight his jeans were feeling in the crotch department. If he wasn't kissing Cas senseless within the next five seconds he would go completely insane. "You know…Anna was right about you, you really are a decent guy." Cas mumbled with a smile still on his lips. Dean blinked for a moment then his heart sunk as he remembered Anna. The sister of the guy Dean was now seriously thinking about kissing senseless and the girl he was seeing. God, he was such a fucking asshole. "Don't let that compliment go to your head though Hollywood Ken you still make some shit films." Cas added closing his eyes.

"Thanks Cas..." Dean mumbled removing his hand from Castiel's chest. He lifted himself up off the bed and gave Cas a small, sad smile. "Go to sleep Cas, I'll see you in the morning." Dean added walking out the room and towards the couch where Jo was passed out and snoring ever so slightly. Knowing she'd get a terrible crick in her neck if she carried on sleeping there much longer Dean easily picked her up and carried her to the spare room where she always crashed when drunk.

"Dean am I walkin'?" Jo mumbled sounding slurred.

"No, you're flying angel." Dean said trying not to sound too sarcastic.

"That's nice…Dean, my mouth tastes like a bar floor..." Jo mumbled.

"Yeah that'll happen when you drink most of my booze." Dean said chuckling slightly as he stopped in the spare room. "We're coming in for a landing Jo." Dean added.

"That's nice. You're nice Dean…Cas' is nice… Jo mumbled.

"Yeah…yeah he is." Dean said placing Jo on the bed and tucking her in.

"Tonight has been nice…" Jo said quietly.

"Yeah it has Jo." Dean said as he made sure Jo was comfortable.

"You seemed happy tonight…that's nice." Jo then said still sounding quite slurred. "It's nice that you're in love." Jo then said

"What?" Dean asked wondering if he had heard Jo correctly.

"The look…you're in love…it's…it's nice." Jo mumbled.

"Jo…"

"Yes?"

"Stop saying the word 'nice." Dean said with a small chortle because that was the easiest thing to say to her at the moment. Hopefully she was drunk enough to not remember any of what she had said once she woke in the morning.

"Sorry Dean." Jo mumbled.

"Go to sleep Jo." Dean said as Jo burrowed herself into the bed.

"Ok Dean" Jo said as she gave Dean a small drunken smile then swiftly went back to sleep.

"Goodnight Jo" Dean said quietly giving Jo a kiss on the forehead then walking walk into the main living area of the apartment. Seeing as Cas was fast asleep in Dean's bed, Jo was in the spare room and Dean could hear Sam snoring loudly from his own room it seemed that the couch was the only place for Dean to sleep even though all he wanted at that moment in time was to be in his bed with Cas lying next to him.

As he lay on the couch he realised that he needed to go back to Chicago. He had to. He needed to sort things out with Anna because now he was beyond confused about everything going on in his life. He'd nearly kissed. God, he'd wanted to kiss him so fucking much and it was only Castiel saying her that Dean remembered that Anna even existed. God he was in fucking trouble.

* * *

**Author's Note: Hey hey guys. Huge thanks to everyone who is reviewing this fic, it really means a lot that so many of you love it. **


	11. Chapter Eleven

**Chapter Eleven**

Dean woke with the largest crick in his neck when he woke up. How was it possible that Castiel's damn couch had been more comfortable than Dean's? He rolled off the couch and dragged himself towards the general direction of the kitchen. The kitchen was where the coffee was so that was where Dean was going. Dean opened the cupboard to grab a new pack of coffee and as he did so he heard movement coming from Sam's room.

"Wow, you look like shit." Sam said when he walked into the kitchen.

"Thanks bitch...I'm not going to make you coffee now." Dean muttered holding up the pack of coffee.

"I'm just saying; you look like you didn't get any sleep last night." Sam said shrugging.

"Yeah well the couch is uncomfortable as fuck." Dean muttered grabbing a new filter for his coffee machine.

"I thought Jo was on the couch." Sam said sitting down at the breakfast bar.

"No, I put her in the spare room...Cas...Cas had my bed." Dean said. Sam raised an eyebrow but didn't say anything which pissed Dean off more than it should have. It was almost as if Sam knew that Dean had nearly kissed Castiel last night and that drove Dean up the wall.

"You and Cas…"

"What about me and Cas?" Dean asked hating how defensive he sounded.

"I was just going to say that you and Cas seem to get on really well, that must be nice what with you seeing Anna." Sam said but Dean could see it, he could the words that Sam wasn't saying in his eyes and that terrified Dean. It really did. "He's a really decent guy, you're lucky he doesn't think that you're that much of a jerk."

"Thanks." Dean muttered sarcastically because he honestly wondered if Castiel still thought he was a jerk actually. It wouldn't surprise him.

"So when are you getting the plane back to California?" Dean asked Sam has he poured coffee into two large mugs. Sam had been in New York for a few days to see Dean and to find a gift for Jess' birthday that was in two days. Sam had agonised for days trying to find the right gift before he found a first edition copy of Jess' favourite book in a small second hand bookstore.

"I'm leaving in about an hour." Sam said. "What about you, what are you going to be doing?" Sam then asked before he took a sip of his coffee.

"Well…I'm going to drive to Chicago." Dean said shrugging and Sam choked slightly. "It's not that big of a deal Sam. Cas needs to get home and I need to see Anna so I might as well drive." Dean said shrugging even though the thought of sitting in a car for twelve hours with Cas was heavily playing on his mind.

"I'm not saying anything."

"Yes you are. Both you and Jo have that incredible talent where you can put whole sentences into just one blank look."

"Ellen taught us well."

"Well I must have missed those lessons."

"You were most likely in detention for punching someone." Sam said grinning over at Dean. "Does Cas know that you're going to be driving him to Chicago?"

"No…I decided it last night when I was going to sleep."

"Well you can tell him now." Sam said nodding over to Dean's bedroom door. Dean glanced over his shoulder and was immensely glad that he wasn't holding anything because it probably would have ended up on the floor.

Castiel emerged from Dean's room and it took everything inside of Dean not to just walk up to Castiel and kiss him fiercely on the mouth. He looked so sleepy and rumpled in just his t-shirt and boxers with his hair a complete mess and his full lips parted in a yawn. As he stretched his arms up high his t-shirt lifted and Dean became fixated in the strip of skin visible. There was the strongest urge inside of him to run his hand across it just so he could feel the warm skin again.

"M-m-morning." Castiel muttered blinking several times as he walked towards the open kitchen. "Please tell me that there is a copious quantity of coffee." He said pleadingly. Dean quickly poured him a mug and handed it to him with a small smile. Castiel wearily smiled back before gulping down his coffee like his life depended upon it.

"Wow, Dean and Jo can barely form sentences when hung over let alone use three syllable words."

"I could quote Dickens, Hemingway or Scott Fitzgerald but my head hurts too much to be perfectly honest." Castiel muttered and dean was very grateful that he didn't quote an author because the memory of last night, of Castiel's lips speaking a beloved quote had nearly sent Dean over the edge. He would not be able to resist the temptation to kiss Castiel again even with his brother in the damn room.

"Well I best get my stuff together. I'll leave you two to your coffees and whatnot." Sam said rising from his seat and exiting stage right. Dean glared at the back of his brother's head as he sauntered off into his own little room to pack. Damn Sam…

"Um…how's the head this morning then?" Dean asked trying to sound casual.

"It's been worse; I think I was just so damn tired last night. I barely remember getting back here let alone going to sleep." Castiel said and Dean was instantly relieved. Castiel wouldn't remember the way that Dean's hand had lingered on either his stomach or his waist. He wouldn't remember that Dean had nearly kissed. Ok part of him was slightly upset that Castiel didn't remember but it was for the best in the long run he guessed.

"Think you can manage breakfast? I don't have Pop Tarts but I could make you something like a bacon sandwich or an omelette." Dean said.

"Food certainly sounds like a very positive thing right about now so thank you." Castiel said sitting down in the seat Sam had vacated while he watch Dean set about to make food. Dean was just getting ingredients from the fridge when there was noise from the guest room.

"Jesus fucking Christ, Mary and Joseph combined…" Dean heard someone, and by someone he basically meant a groggy sounding Jo, mutter as the guest bedroom door opened. Jo practically crawled out and without a word Dean held out a large mug full of coffee for her. Jo reached out for the mug then carried on her way to the bathroom. The door shut with a close and Dean couldn't help but snort.

"Is she ok?" Castiel asked sounding highly concerned.

"Yeah, she'll be fine. If she's not out in an hour though I might have to go and check to see if she hasn't drowned in the bathtub" Dean explained as he went back to making breakfast. Sam appeared after twenty minutes and announced that he'd be leaving as there was apparently heavy traffic towards the airport so he would need to leave now and save missing his flight. Dean watched as Sam gave Castiel a warm looking one armed hug.

"It was really good to meet you Cas" Sam said grinning while Castiel went slightly red. Dean resisted throwing a frying pan at his brother…thought it was highly tempting. "Is Jo conscious?"

"She's in the bathroom." Dean said.

"Yo! Jo! I'm leaving now!" Sam called in the general direction of the bathroom.

"Bye Bigfoot! Say happy birthday to Jess for me!" Jo's yelled groggily.

"Well at least we know she's alive still." Dean said as he walked over to hug Sam even though his brother was acting like a child over Castiel being there. "See you soon bitch. Give Jess a birthday kiss from me."

"Yeah I will. See soon loser." Sam said giving Dean a grin before he picked up his duffel bag. "See you Cas."

"Bye Sam." Castiel said giving Sam a wave of his hand. Sam gave Dean one last smile before he hurried out the apartment leaving Castiel and Dean alone in the kitchen. Dean went back to making breakfast while Castiel drank his coffee.

"So...um..." Dean heard himself mutter as he handed Castiel his breakfast.

"You really can't say anything unless it's written for you in a script can you?" Castiel asked with that damn smirking smile of his.

"Funny. I was going to say that instead of you getting the train back to Chicago how...how about I drive?" Dean asked.

"To Chicago? You don't have to do that Dean."

"You know me, I never miss a chance to drive for several hours at a time...besides I could do with seeing your sister." Dean said and he watched Castiel's face falter for a second before it was replaced with a blank look that Dean found impossible to read.

"Yeah...of course you do. If you want to drive then drive." Castiel said shrugging his slender shoulders.

"Road trip!" Dean heard Jo cry from the bathroom and he groaned inwardly.

"You could always ditch her on the Brooklyn bridge." Castiel said.

"Don't give me any ideas." Dean said glad that Castiel's face had changed from the blank look to that of a slight smile.

* * *

"Jo if you're coming with us then hurry up, it's a twelve hour drive to Chicago!" Dean yelled nearly an hour later. It was ten in the morning and Jo was still pissing around in the guest room. If they didn't leave soon they wouldn't get to Chicago until past midnight.

"I'm coming!" Jo yelled from the guest room. Dean couldn't help but roll his eyes as Jo came running out the room with her bag bulging. "What? I didn't know what to take with me so I just threw in all the clothes that I have lying around here." Jo said.

"Well come on then." Dean said before he turned to Castiel. "Are you ready?"

"Yeah sure, I've text Anna telling her what's going on." Castiel said with a small smile as he picked up his messenger bag. Dean didn't want to admit that spending twelve hours in a car with Castiel, plus Jo but she would spend most of the journey asleep in the backseat, was probably going to be the highlight of the next days for him.

* * *

After several hours of being sat in Dean's car Castiel could safely say that he knew all the words to several ACDC songs thanks to Dean's albums. His legs were also beginning to go stiff and he could have done with doing something…anything. He was contemplating texting Anna when he saw Dean yawn slightly.

"You know…if you're tired I could drive for a bit. You could get some sleep if you wanted." Castiel said because he was too wired to sleep and if he was driving then he would at least stop looking at Dean so often. Dean glanced over at him in surprise.

"I thought you didn't drive." Dean said.

"Just because I choose not drive doesn't mean that I don't know how to drive." Castiel said smirking. When he saw Dean's dubious look he smirked even more so. "Afraid I might crash your baby?" Castiel asked.

"Honestly? Yes, but I could do with some damn sleep." Dean said as he began to pull over. As Castiel climbed out the car he heard the bones in his legs creak loudly. He stretched his arms above his head before sliding into the driver's seat. When Dean climbed into the passenger's seat he looked pretty uncomfortable.

"You're not used to people driving your car are you?"

"No not really, she's my baby you see." Dean said. The love in his voice when he spoke about his car was the same kind of love that was in Castiel's voice when he spoke about his favourite books or his laptop.

"Well I feel honoured." Castiel said shooting Dean a smile which Dean quickly returned.

"You should do." Dean said as Castiel started the car back up.

"You…you don't mind if we play some of my music do you?" Castiel asked after a moment.

"Driver picks the music, shotgun shuts their cakehole. That's the general rule when in my baby. It stops Jo from complaining when I play a shitload of Led Zepplin." Dean said.

"Ok…um…my iPod is in my messenger bag." Castiel said nodding over to the bag by Dean's feet. Dean pulled it out and held it up for Castiel. "There's a playlist entitled 'Road Mix', if you don't mind we could play that" Castiel added when Dean handed him his iPod.

"I find it amusing that someone who never drives anywhere would have a road trip mix." Dean said was he watched Castiel plug his iPod into the radio/CD player. Castiel wished he'd stop staring at him because it was making it difficult to concentrate on driving.

"Ok it's more of a 'Sat On A Train Listening To Anna Talk About How Hemingway Stole Picasso's Girlfriend For The Hundredth Time' than a road trip mix." Castiel explained.

"Did he?" Dean asked.

"Who, Hemingway? He may have but that's not the point. Anna just likes to needle me about my favourite authors because I dislike some of her favourite artists." Castiel said with a shrug before the car filled with music. Castiel watched as Dean's face changed from slightly sleepy to completely perplexed.

"Ok, what the hell are we even listening to?" Dean then asked looking at Castiel's iPod with a terrified look on his face.

"They're a British band called Mumford and Sons. Haven't you heard of them? They're pretty big over here in the US, they're very good as well" Castiel said smugly.

"They're playing banjos Cas, banjos!" Dean cried.

"You need to broaden your horizons Dean." Castiel said haughtily as he shrugged his shoulders again. Dean looked at him then shook his head with a loud groan before pouting. Dean's love for old rock was actually quite adorable if Castiel was being honest.

"Banjos belong deep in the south with the red necks, not in my car." Dean then said still pouting dramatically.

"'Driver picks the music, shotgun shuts his cake hole'" Castiel quoted grinning at Dean and the look on Dean's face was priceless.

"God you're such an asshole..." Dean muttered under his breath and Castiel couldn't help but chuckle. "I hate you" Dean groaned. "I can't believe I'm actually letting anyone drive my baby let alone make me listen to this." He added.

"The musical education will be good for you." Castiel said and Dean just huffed in his seat as if Castiel had seriously insulted him. Castiel continued to drive as they sat in silence until the next song came on and Dean glanced over at Castiel questioningly.

"It's Bastille, they're another British band." Castiel explained.

"Ok I'll admit they aren't that bad..." Dean said begrudgingly. "I still can't believe I'm letting someone drive my baby though never mind how tired I am."

"Well I've never crashed a car yet so you shouldn't be so worried. I've even driven one handed and very distracted before." Castiel said with smirk. He wasn't really going to mention hand jobs in front of Dean because...well he was Dean Winchester but the temptation had been too great and the look on Dean's face now was far too amusing. Plus Dean seemed so tired that he probably wouldn't even remember this conversation.

"What were you doing?" Dean asked warily.

"Something that required one hand and my concentration." Castiel said winking at Dean. Dean's eyebrows shot up as he clearly understood exactly what Castiel was talking about now. Castiel wasn't sure why he was telling Dean this, maybe it was to shock him or maybe it was to prove to Dean that he wasn't the nerd or the prude that Dean might have thought he was. Instead of looking shocked Dean simply smirked.

"Was it the coffee or the looks that got them?" He asked in a low husk that sent a rush of longing deep down into Castiel's chest. He should stop this now, stop this friendship that was forming between he and Dean, because it would just end in heartbreak once Dean went back to New York or he made things real with Anna. This was dangerous territory and Castiel knew he should stop but instead he gave Dean the dirtiest smile he possessed.

"Maybe it was both. It's how I get everyone in the end." He said waiting to Dean's face change, waiting for the weight of Castiel's words to sink in but it never came. Dean just carried on looking at him with a delicious smirk and, holy fuck, he winked. Dean must have more tired than Castiel originally thought. That was the only explanation right?

That didn't explain last night though. That didn't explain Dean's hand on his waist or the fact that at one point while they were sat on Dean's bed Castiel thought that Dean was going to kiss him…

* * *

After several more hours Dean took over driving duties and the music changed from Castiel's to Dean's favourite classic rock songs. Dean seemed relieved to be listening to music where banjos weren't the main instrument used. Jo would occasionally wake up in the backseat to offer some sarcastic comment before Dean told her to go back to sleep and stop being so annoying.

"I find it amazing that she can sleep in the car, I never can." Castiel said glancing to the back of the car where Jo was snoring slightly.

"She used to get carsick really badly when we were kids and the only thing that helped was her going to sleep. You only have to get her sat in the passenger seat of a car nowadays and she's falling asleep." Dean explained. "She once slept for fifteen hours straight when we were driving across America one summer."

"That must be nice in a way."

"Well it stops her from blowing chunks on the highway so yeah, I guess it is nice."

"You're so poetic Winchester…" Castiel muttered with a shake of his head.

"As always your condescension is always appreciated Milton." Dean said firing a quick smirk at Castiel. Castiel really wasn't sure if Dean knew that this all felt like flirting and if he did then Castiel really wished that he would stop because it wasn't helping matters at all. He also wished that Dean would keep his eyes on the road more often because wasn't that one of the damn fundamentals of driving?

Castiel felt his phone buzz in his back pocket and it took him several moments to pull it out of his pocket. Glancing down at the screen he was surprised to see a text message alert from Gabriel. This could not be good at all and Castiel couldn't help put let out a slight groan.

"What's wrong?" Dean asked when he heard Castiel's groan.

"It's a text from Gabriel." Castiel said rolling his eyes as he unlocked his phone.

**Gabriel: **Where you be at big brother?

"That is terrible grammar and I'm ashamed to be related to him." Castiel muttered shaking his head.

**Castiel: **I'm driving back from New York.

**Gabriel: **There are so many random things about that sentence, I hope you know that. Do you fancy making a detour to Lincoln to pick me up? My weekend is free and it's going to be very boring just sat at home. So do you feel picking up your favourite sibling?

**Castiel:** Anna isn't in Lincoln at the moment.

**Gabriel:** Very funny. Please come to Lincoln and pick me up.

**Castiel:** Did you just say please?

**Gabriel: **Yes, yes I did so come and pick me up.

"Do you mind if we make a detour?" Castiel asked Dean.

"How much of a detour?" Dean asked glancing at the clock on the dashboard.

"To Lincoln, it's not that far from here. Gabriel wants to come to see Anna and I for the weekend." Castiel explained. Dean shrugged his shoulders.

"I don't mind." He said. "We can pick him up if you give me directions."

"Yeah sure, of course" Castiel said as he began to type his reply.

**Castiel:** Fine, we'll be there in a few hours.

**Gabriel:** We?

Castiel refused to answer because it would be easier to not tell Gabriel via text messaging that he was in a car with Dean Winchester.

**Gabriel:** Who's 'we'?

**Gabriel: **Castiel?

**Gabriel:** Fine, I'll find out soon enough anyway, you dick.

* * *

The journey into Lincoln took less time than Dean thought thanks to the little amount of traffic on the road. Not before too long Castiel was navigating him down a quiet looking street filled with houses. Dean killed the engine in front of the house Castiel told him to park in front and looked up at the house.

"Wow…nice house." he said when he pulled up outside the medium sized house with a huge front lawn.

"It's my Aunt and Uncle's house." Castiel said without added anything else as a way of explanation. Dean looked at his face and was surprised to see how sad it looked, like this house held too many memories almost. "I won't be a minute." Castiel then said climbing out of the car and slamming the door behind him. The loud noise jolted Jo in the back seat and she mumbled something groggily.

"What?" Dean asked turning around in his seat.

"I said 'Where the fuck are we?'" Jo muttered yawning loudly.

"Lincoln." Dean said.

"And where exactly is that?" Jo groaned between another loud yawn.

"Two hours from Chicago, we're picking up Castiel's brother." Dean said nodding towards the house. Jo sat up in her seat and looked towards the house. Dean followed her lead and could see Castiel at the front door waiting for someone by the looks of it.

"More siblings?" Jo asked raising an eyebrow.

"Just the one, his name is Gabriel." Dean explained.

"As in the angel?" Dean nodded his head "Seriously?" Jo asked with a loud snort.

"Seriously so don't take the piss." Dean said looking back at Jo and giving her a warning look.

"When do I ever take the piss?"

"When do you not?" Dean pointed out. Jo clearly thought about it for a moment before she nodded in agreement. "Right, so be nice…or at least your version of nice." Dean said glancing back over towards the house. Castiel was now stood on the doorstep talking to a very excited looking Gabriel. Even from here Dean could see Castiel exasperation at his brother while he seemed to explain something. At one point it looked like Gabriel was going to race back into the house but Castiel grabbed him by the collar and pushed him towards the driveway. A woman who looked like she was in her early fifties came to the door and gave Castiel a tender smile before waving both Castiel and Gabriel goodbye. The two bothers carried on marching until Castiel reached the car door.

"I am so very, very sorry for whatever will happen within the next two hours." Castiel said Dean once he was back in the car.

* * *

Jo was whinging in the back seat, which Gabriel, who was sat next to her, somehow found more amusing then it was. Castiel had warned Dean that once they picked him up Gabriel would probably try to get into Jo's pants no matter of the age difference and that seemed pretty evident by the countless compliments that Gabriel was giving her. Castiel had called him incorrigible and Dean sensed that was pretty accurate. They had been in the car mere minutes and this had already started. While Castiel seemed to be having difficulty refraining himself from kill his brother Dean was having his own difficulty trying to find something decent on Castiel's iPod so he could have done without the distraction of Gabriel trying to flirt with Jo.

"Christ, there has to be shitloads of tracks on here." Dean muttered trying to keep his eyes on both the road and the small iPod screen.

"Is that the official way to count music these days?" Gabriel asked chuckling.

"Dean close the window, I'm freezing. Why is Illinois so fucking cold?" Jo complained. Dean sighed as Castiel reached over to the middle by the gearstick and rolled up the windows so Dean could carry on looking for a good song.

"Awww Castiel to the rescue" Gabriel said clapping his hands.

"Seriously Cas, how many songs are on this thing?" Dean asked ignoring Gabriel which seemed like the easiest thing to do.

"By my last count I think it was two thousand, three hundred and eighty six...no wait, ninety four. I added a new EP onto it two days ago." Castiel said.

"That's insane." Dean said rolling his eyes. "Oh I give up. I cannot find a single band I've actually heard of." Dean complained handing the iPod back to Castiel.

"So you're giving up music rights?" Jo asked. "Wow..." She said emitting out a low whistle.

"Shut it Jo." Dean muttered because there was way too much context within that whistle.

"You wear too many flannel shirts not to know half of these bands Dean." Castiel said picking a song at random and guitar music soon filled up the car.

"That's because he's a mid-western farm boy. Wearing flannel is a rule and has nothing to do with music. Besides his taste in music is shit" Jo said snorting.

"For the last time, I did not grow up on a farm! Jo you constantly forget that you lived down the street from me until we were seventeen?" Dean snapped.

"I like to say it because it pisses you off." Jo said shrugging. "It's one of my favourite pastimes along with 'See If Dean Can Have A Fit Over His Coffee Table' and 'Replace His Face Cream With Mayonnaise'" Jo explained.

"Face cream?" Castiel asked raising an eyebrow at Dean.

"It's moisturiser and I have sensitive skin ok?!" Dean said feeling his face grow red.

"You know, I could imagine you on a farm Dean. Straw in your mouth, strategic overalls, working on tractors, doing whatever it is they do with hay...tipping a cow. That should be your next movie! I could see it selling very well."

"Cow tipping is something you're not supposed to do on a farm Gabriel." Castiel said rolling his eyes at his brother.

"Dean got arrested for cow tipping once." Jo said grinning from ear to ear. "We were thirteen and Dean was bored one night so along with some school friends we went cow tipping. It was great…until Dean got caught that is. Pamela has expressed many times that he should not mention it in any interviews he gives."

"See! I knew you'd do well on a farm!" Gabriel said clapping his hands. Dean almost considered driving his car into the nearest tree or street light but he just couldn't do that to his precious baby.

"The next person to mention farms, straw or cows can walk the rest of the way to Chicago." Dean growled firmly keeping his eyes on the road.

"What about hay?" Gabriel asked leaning over Castiel.

"Especially hay!" Dean cried. Jo and Gabriel stifled snorts of laughter while Castiel smirked in his seat. It was going to be a long night.

* * *

The two hour trip didn't drag half as much as Dean thought it would. It probably helped that he placed a ban on talking after forty minutes as well Castiel stopped trying to play obscure music and settling on playing some relatively decent rock music.

Jo had fallen asleep again though Gabriel didn't seem to mind at all seeing as her head was resting on his shoulder. His smug smile was so huge Dean wondered if it hurt to smile like that. Castiel just shook his head at his brother and Dean was quickly seeing that this was the main Castiel did when it came to Gabriel. Castiel seemed highly relieved when Gabriel dropped off to sleep when they were about thirty minutes away from Chicago.

"Um…" Dean said coughing slightly to clear his throat. "So…last night was fun." He said.

"Yeah, yeah it was. I can see why you love Jo and Sam so much, they're great people. Sam is very smart; I can understand why you're so proud of him." Castiel said looking over at Dean. "Jo seems like the life and soul of the party as well. Remind me that she and Ruby should never meet, I think it might cause the apocalypse." Castiel added with a quiet laugh as to not wake Gabriel or Jo.

"Yeah…yeah they're my best friends…I couldn't imagine being without them."

"I understand that. I mean, I obviously don't have that relationship with Gabriel but I do with Anna."

"Yeah…you and Gabriel…I'm amazed you haven't killed him yet." Dean said.

"Yes well Gabriel…he's Gabriel…" Castiel said.

"Was everything ok between you two earlier on?" Dean asked and Castiel gave him a questioning look. "When we picked him up in Lincoln, you seemed annoyed at him…" Dean said as the song that was playing changed to a slow track full of deep guitars. Dean wished that Castiel would change the track because it added more to the atmosphere inside the car than necessary.

"Oh that was just him being Gabriel. The thought of being in a car with 'Dean Winchester' was enough to send him into a miniature freak out. If I hadn't of dragged him to the car then he would have gone to get his limited double disc collector's edition of _The Extraction Point_ for you to sign." Castiel said.

"Are you sure that's it?" Dean asked because it seemed like there was something else that could be upsetting Castiel.

"It's…Gabriel has been getting into trouble at school recently and it's been upsetting my Aunt Rachel. Gabriel…Gabriel is her favourite because she thinks he's got hidden greatness so to see him get into constant trouble upsets her…the last thing I want is for Aunt Rachel to be upset."

"Are you close to your Aunt?" Dean asked.

"Yeah…it's a long story Dean." Castiel said and the lowness of his voice made it clear that Castiel didn't want to carry on with the conversation.

"Sorry…I shouldn't have asked should I?"

"It's fine Dean…really, it's fine." Castiel said waving Dean away slightly. With just the wave of a hand Dean felt a millions miles away from Castiel. Castiel had said that things were fine yet it didn't feel like things were fine at all. It seemed that was much as Dean wanted to know more about Castiel the more Castiel pulled away after he'd revealed something about himself. "You need to take the next exit; it'll cut the journey down by fifteen minutes." Castiel then said nodding towards an exit coming up.

* * *

"Welcome home!" Anna cried to Castiel when she opened the door to the apartment. "I see you've brought Gabriel as well...I'll hide all the flammable objects." She added when seeing Gabriel's slightly sleepy but happy face. Dean couldn't help but chuckle at the sheer look of panic in Anna's eyes when she saw Gabriel.

"Oh dear sweet sister you think too ill of me." Gabriel said.

"No Gabriel, I don't think ill enough, my room at home still has scorch marks on the ceiling thanks to you." Anna said before she kissed Dean on the cheek.

"That was an accident!" Gabriel said innocently not convincing anyone.

"Oh I like this kid." Jo said snorting before she turned to smile at Anna. "Hey there, you must be Anna. Both Dean and Castiel have told me all about you."

"Jo right? Dean's told me about you as well. It's really nice to meet you." Anna said.

"See? People are actually happy to see me." Jo said smirking over at Dean. Dean rolled his eyes and refrained from making a highly sarcastic comment but from the look on Castiel's face he could tell how much Dean wanted to make a highly derisive remark towards Jo.

"Sorry I'm back so late…we had to make a detour thanks to Gabriel over there." Castiel said.

"It's fine. You just missed Ruby actually."

"What a shame." Castiel said sarcastically.

"She's having a party tomorrow night and she's hoping to 'seal the deal' with some Philosophy major she's had her eye on for the past week" Anna explained and Gabriel looked crestfallen despite the fact that he had just spent the best part of two hours trying to flirt with Jo. Castiel was right when he had called his brother incorrigible.

"Well…not that this conversation isn't riveting, because it is, but I could do with my beauty sleep. I'll go and set myself up in Castiel's bed." Gabriel said smugly.

"No you won't." Castiel snapped quickly. "You can have the damn couch and be grateful" Castiel added.

"You don't have to worry about us, we won't crash here. Jo has a deep and resounding love for motels." Dean said quickly because he didn't want Castiel or Anna to worry about where he or Jo was going to sleep. Gabriel raised his eyebrows suggestively and turned to look at Jo with a leering smile.

"Really?" He asked looking Jo up and down. Dean could see Castiel shaking his head in frustration off to the side.

"They're fascinating places ok? It's like watching theatre sometimes. I've seen some incredibly interesting things in motels in my time." Jo said grinning. While Jo 'fascinated' Gabriel and Castiel with past stories of sights she had seen in motels Dean walked over to Anna who smiled at him brightly. It was a nice sight and yet it made Dean feel even more guilty about the night before and the near kiss.

"Hey." Dean said taking Anna to one side. "Are you free tomorrow afternoon?" he asked. He'd come here to talk to Anna, to try and see if he could make things work so that's what he had to do he guessed.

"Yeah, yeah I'm free." Anna said.

"Great…um, do you want to grab a coffee or something?" Dean asked and Anna nodded slightly.

"Yeah, I should be free around two so shall we meet at the café near here?" Anna asked.

"Yeah, that sounds great. It's getting late so Jo and I should probably get out of your hair." Dean said.

"You don't have to." Anna said.

"We probably should, we still have to book into a motel room."

"As long as you're sure. Thank you for driving Castiel back here…it was really kind of you."

"It's fine Anna, it really is." Dean said not wanting to say that he'd enjoyed himself far too much being sat in the car with Castiel.

"Well I guess I'll see you tomorrow then? Two?"

"Yeah." Dean said giving Anna a quick smile before looking over to Jo. "Oi, Harvelle!" He called. Jo looked over to Dean and gave him an innocent smile that scared Dean far too much.

"I wasn't telling Gabriel about the time you nearly fell off that motel balcony when we were in Little Rock!" Jo said. Dean couldn't help but roll his eyes at her. Why was he even still friends with her?

"Yes well thanks for that, we best get going if we're going to get into a motel." Dean said and Jo nodded her head. Giving Gabriel a wink she sauntered over to Castiel and gave him a quick hug.

"Despite your musical taste, which is even more questionable than Dean's, you were a very good traveling buddy Cas." Jo said. "And I'll see you soon" she added winking over at Gabriel. God she must have been tired if she was flirting with a high schooler despite the fact that she had spent the best part of the last fourteen hours asleep.

Dean shot Castiel a quick smile which Castiel returned though he looked somewhat dubious for a moment. Talk about mixed signals. "I guess we'll see you guys tomorrow" he said before he and Jo left the apartment and walked down to the impala. Jo yawned loudly as they were climbing into the car. Dean turned the engine on as Jo yawned loudly yet again. As Dean was pulling out of his parking space he noticed Castiel's iPod still plugged in. "Put it on the dashboard will you?" Dean asked as he glanced down the road to make sure there was no traffic.

"Since when did you go digital with the old tunes?" Jo asked.

"I didn't, it's Cas'." Dean said with a shrug. "Cas plugged it in when he was driving. See you miss things when you're passed out in the back seat." Dean added and Jo raised her eyebrows in surprise.

"You let Cas drive the baby?" Jo asked whistling. "When's the wedding?" Jo then joked.

"What does that mean?" Dean asked.

"Come on Dean, I've known you since we were in diapers. I was the one who got their drivers licence first, and on the first try as well. Without killing anything."

"That deer came out of nowhere!"

"Yeah whatever. We've been friends since the days of apple juice in sippy cups and you've never let me drive the baby."

"You totalled two cars last year." Dean pointed out. "Both of those cars I brought you as well"

"The totalling of the cars is a matter of opinion."

"I would call Bobby's opinion a strong one." Dean said. Jo gave him the finger.

"You must like him." Jo said after a moment.

"Who?"

"Cas"

"He's the brother of the girl I'm seeing...sort of. I have to like him." Dean said.

"His iPod is in your car, the car that he drove despite you not letting anyone drive the Impala."

"He forgot his iPod, that's all."

"You let him drive, you have to like him." Jo pushed and Dean really wished that she would stop talking.

"I had been driving for hours and Cas offered to drive for a while so I could get some sleep, that's all."

"Ok"

"Ok?"

"Yeah, ok...for now anyway."

"Jo I'm warning you."

"I'm not saying anything. Yet."

"Jo come on..."

"There is something you aren't telling me Dean, I know there is something you aren't telling me." Jo said sternly crossing her arms over her chest and glaring at Dean with a steely look. "Why can't you just tell me? We tell each other nearly everything."

"I nearly kissed Cas in New York." Dean hear himself say before he could stop himself. Whenever Jo looked at him like that he found himself being more honest than he wanted to be, damn Jo.

"I knew it!" Jo yelled causing Dean to nearly crash the car.

"Jesus Jo!" Dean cried slamming on the breaks and incurring a blare of a horn from the car behind.

"I knew it though! The next day you were so jumpy and you seemed so pissed off! What stopped you from kissing him? He'd clearly be into it. He looks at you like you're naked and covered in melted chocolate." Jo said sounding smug.

"Because he mentioned Anna ok? I like Anna and it is not fair to drunkenly kiss her brother when I like her." Dean said with loud sigh.

"You like Cas though, I saw that as soon as I met him." Jo said.

"Yeah I do like Cas; he's sarcastic and a bit of dickhead without being a complete asshole about it. I've never met anyone apart from hom who is so snarky towards me."

"What about me and Sam?" Jo asked.

"You and Sam are family, Cas is...Cas is Cas. He's...different." Dean said knowing that didn't half explain Cas but Dean didn't think his words could do Cas justice.

"He's going to be assbutt naked screaming your name by the end I the month." Jo said bluntly.

"Jo I'm warning you..."

"Yeah, yeah, yeah I'll shut up now...as long as you admit you're not thinking about Cas being assbutt naked screaming your name."

"Shut up Jo." Dean said tersely because he really couldn't stop thinking about the imagine Jo had planted in his head. It wasn't a bad image really.

"You should tell him how you feel." Jo said shrugging her shoulders.

"That I want to see him 'assbutt naked'? Yes because that is a conversation I want to have." Dean said with a voice weighted down with heavy sarcasm.

"Well talk to Anna then."

"Are you insane? You want me to talk to Anna about how I nearly kissed her brother?"

"I'm just saying, maybe Anna will understand if you just explain. You like her sure but you also like Cas, see how she feels about you and then if she likes you but not in a way that could last then say something to Cas."

"That is the worst idea ever Jo."

"No it's not. It's a great idea but you just don't want to do it because you're a fucking pussy."

"Gee, thanks Jo."

"It's true, Sam agrees."

"Wait...what?! How the hell does Sam agree with you? When did Sam agree with you?"

"When I was aboard the moose express. We had a lovely conversation."

"What does Sam know?" Dean asked. He'd spent a lot of time hiding things from Sam so finding out that Dam knew there was something between him and Cas was discomforting.

"That you and Cas fuck the hell out of each other with your eyes at every opportunity! Seriously Dean you were so fucking obvious back in New York! Sam and I were shocked to find you asleep on the couch and not with Cas. You really do need to give Sam more credit; he's not stupid, he can clearly see something between you and Cas." Jo said sternly.

"Jo-"

"Don't tell me to shut up Winchester. Sam doesn't care about who you care for, he just wants you to be happy." Jo said as they pulled up outside a motel. "Now just promise me that you'll talk to Anna and Cas? Because if you don't then you'll really regret it."

"Jo think about what you're talking about, can you imagine the shit fit Pamela will have over his if she found out that I like Cas."

"Oh for fuck sake Dean! Pamela has controlled your life in nearly every single way since you were nineteen! You're happy ok? I watched you when we were out with Cas and the way you look at it! He makes you happy so do something about it before I punch you in your fucking face!" Jo snapped slapping Dean repeatedly on the arm.

"Ow! Will you stop that?" Dean snapped back.

"No! Not until you promise me that you'll stop being such a fucking pussy!" Jo said.

"Fine! I'll talk to Anna."

"And you'll talk to Cas?"

"Jo don't push it." Dean said parking up in the small parking lot. "I'm fucking exhausted so if you're planning on carrying on with this rant then you can sleep in the bathroom."

"Wouldn't be the first time." Jo said as they climbed out the impala. "Seriously, why is this city so fucking cold?" Jo grumbled to herself as they walked into the motel.

"Jo if you don't stop complaining then you can forget sleeping I bathe bathroom, I'll make you sleep outside in the hallway." Dean threatened.

"Butt naked Cas." Jo said with the smirk.

"I really hate you sometimes" Dean muttered.

* * *

Dean met Anna the next afternoon in the small café near Anna's apartment and he honestly didn't know what the hell to say to her. He knew he couldn't tell her about the near kiss in New York no matter what Jo had said to him. He was sure that it would just be cruel and the last thing Dean wanted to be towards Anna was cruel. Dean was there first and grabbed the most inconspicuous table there was. He only had to wait a few minutes before Anna arrived, shaking drops of rain from her red hair. She smiled when she spotted Dean and quickly moved between the tables to reach Dean. He stood up to give her a quick kiss on the cheek because that was the polite thing to do.

"You haven't been waiting long have you?" Anna asked as she sat down opposite Dean.

"No, I've only just gotten here." Dean said.

"Oh…good." Anna said. "You seemed like you had something that you needed to say last night and that's why you asked me here, am I right?"

"You're pretty observational."

"You have to be growing up with both Castiel and Gabriel though there for both very different reasons."

"Well yeah…I did want to talk to you about something." Dean said before he coughed nervously. Shit, he really should have rehearsed this beforehand because now that he was here he had no idea what the fuck to actually say to Anna. Damn… "I…I wanted to talk to you about…I wanted to talk about us."

"Us?" Anna asked frowning slightly.

"Yeah…as in 'you and me'" Dean said.

"Oh…"

"Oh?" Dean asked because the look on Anna's face was beginning to confuse him as well as make him feel more nervous than he already felt.

"Dean you're an amazing guy..." Anna said holding onto Dean's hand gently. "I'm so glad that I've gotten to know you over the past month or so. Most people in America would think me crazy for doing this but I think I have to…no I know have to. I really like you and I like your friends as well. Jo is lovely and I really hope to keep in touch with her after all this...I really like you but...I think we're better being friends. I don't want my life to be thrown into the spotlight even more so but being friends with you is something I want." Anna said. "I like you, I really do like but it's just...it's...I just don't think I can like you...love you enough for all the attention I'd get from the media to not get to me...and...and well I think you want this to work more because of what your publicist thinks and not how you feel about me."

"Anna-"

"I'm not saying that to be cruel Dean, if anything I'm saying it to be kind because this way we can both find people who really, really care about us. Though, I think if you looked close enough you'd find that person quite quickly." Anna said with a small smile slowly spreading across her lips.

"What do you mean Anna?" Dean asked but Anna just chuckled slightly as she stood up and kissed Dean on the cheek.

"I'm not blind to what is in front of me Dean and neither should you be." Anna said with a small smile "They might not be there forever Dean, so…act quickly ok?" Anna added before walking out of the café leaving Dean highly confused. Did Anna mean what Dean thought she meant and if so then how fucking obvious had he really been?

* * *

The apartment was empty. Actually empty. There was no Anna and no Gabriel. Castiel could just sit on the couch and watch whatever he damn well felt like watching for once. He could eat his own Pop Tarts without someone stealing them. He could sing Johnny Cash as loudly as he wanted without anyone complaining. It was actual bliss. Well it was bliss until there was a knock on the apartment door. If it was Gabriel saying that he'd forgotten his keys then Castiel was going to end up throwing something at him.

Hauling himself up off the couch Castiel walked to the front door and pulled it open, never expecting the person who was standing to actually be standing there in front of him.

"Dean? What are you doing here?" Castiel questioned when he opened the front door to see Dean standing in front of him looking a tad worse for wear.

"Um…hey." Dean mumbled slightly.

"Hey..."

"You weren't busy were you?" Dean asked as Castiel let him into the apartment.

"Not really, no. I'm just revealing in both Anna and Gabriel being out of the apartment at the moment." Castiel said nodding towards the TV that was showing the first ten minutes of one of his favourite films.

"God, Jo came with me to Sundance to see this and she fell asleep fifteen minutes in. I was so pissed off at her."

"Anna's the same. She never lets me put it on if she's in the apartment." Castiel said. "Anna…um…Anna told me about this afternoon. I'm sorry that it didn't work out between you two." Castiel said.

"What? Oh yeah…yeah…thanks." Dean said sighing slightly.

"Do you want a beer or something?" Castiel asked because it seemed like the polite thing to do.

"Um…yeah…sure." Dean said with a shrug. Castiel walked over to the fridge and grabbed two beers from inside. He opened them both then handed one to Dean. "Thanks. I'm sorry if I've interrupted you watching your film."

"It's fine Dean, really. Sit down if you want…no offence but you look like you need to talk…about this afternoon." Castiel said.

"What you mean I could do with talking about the fact that your sister completely rejected me? Yeah I suppose I could do with talking about it." Dean said shrugging. "Maybe it's for the best in the end though." Dean said. "That Anna and I have stopped seeing one another…" he added with a slight mumble. Castiel didn't say anything; instead he just drained the remainder of his beer and placed the empty bottle on the kitchen counter.

"Yeah…I mean you're some famous movie star, you should be dating moronic supermodels or someone like that." Castiel said shrugging because if Dean and Anna were completely over then that meant that the unlikely friendship forming between him and Dean would soon be over. It would actually be a relief in the end, not having to see Dean again in anything but his terrible films. Castiel could pretend that Dean was an asshole and this longing he was feeling would soon disappear.

"No…no I didn't mean it like that Cas." Dean said sternly looking at Castiel with a hurt look in his eyes.

"In what other way could you mean it?" Castiel asked.

"Don't you…fuck…forget it." Dean muttered.

"Forget what exactly?" Castiel asked. If he thought that Dean was going to say what Castiel desperately wanted him to say then Dean needed to say it now.

"No…just forget it. I wasn't going to say anything." Dean said.

"Yes you were, why don't you just say it Dean?" Castiel said beseechingly.

"Because you clearly still think I'm just some arrogant movie star and that's probably the only you'll ever see me." Dean snapped surprising Castiel.

"I don't think that Dean, I don't think that _at all_. If anything I wish you _were_ the conceited bastard I used to think you were because then this whole thing would be a lot easier! I wish you were a complete asshole and not this decent guy who read _The _freaking _Great Gatsby_ just because I happened to say it was my favourite book! I wish you weren't funny and naïve to the good person you are! I wish you didn't like Vonnegut and I wish I didn't have to be so fucking sarcastic and insulting towards you at every opportunity because it is fucking exhausting!" Castiel yelled, his rage boiling over until it seared through his whole body.

"Then why do it? Why be so mocking towards me if it's so exhausting?" Dean asked sounding just as enraged as Castiel felt.

"Because it's less painful than the truth Dean!" Castiel admitted.

"And what's the truth Cas? Because I am dying to know it, I am dying to know why you feel the need to lie to me."

"I truth is that it's too easy to be nice to you, it's too easy to smile at you like you mean everything to me because it's starting to become true! I can't stop thinking about you and it is driving me insane Dean!"

"What?"

"I don't choose to love people Dean, I prefer being alone because then you don't get hurt but I…I couldn't even stop myself from choosing to love you…I need you…I need you to choose me back…" Castiel said and every emotion inside of Castiel drained from his body as he looked at Dean's shocked face. Dean's green eyes were full of confusion and Castiel's heart began to slam against its cage at a rapid speed. It was like he was being hit over and over again by traffic as the seconds slowly dragged on.

Dean's eyes were wide and as the seconds drew on Castiel's heart continued to slam against his chest and he could feel his stomach filling with acid. Dean needed to say something, anything, even if Dean completely rejected him.

"Dean…say something…please." Castiel begged. "Just say _something_…say anything…please" He added. Dean opened his mouth to say something and Castiel swore that at in moment his heart stopped.

* * *

**Author's Note: I'm not entirely happy with this chapter but it's over 9,000 words and I just couldn't write anymore. I might go back when I've finished this story and edit the whole thing just in case. ****There is a cliff-hanger yes but I couldn't help myself. Plus points if you can tell me who invented the term cliff-hanger.**

**I'm always on tumblr so if you feel like leaving abuse over this fic on there then you can find me at .com**

**Castiel's road mix includes the likes of Mumford and Sons, Bastille, Johnny Cash, The Black Keys, Matthew and the Atlas, Kodaline and City and Colour because they are all awesome.**


	12. Chapter Twelve

**Chapter Twelve**

"Dean…say something…please." Castiel begged. "Just say _something_…say anything…please" He added. Dean opened his mouth to say something and Castiel swore that at in moment his heart stopped.

"Oh fuck it" Dean murmured as he pushed Castiel against the nearest wall and Castiel had to concentrate very hard on anything but the fact that Dean Winchester's hands now moving to his face. He tried to think of anything but one of Dean's legs being between his own and he certainly tried very hard not to think about Dean's erection he could feel against his thigh. Before Castiel could say anything lips met his own and he realised that Dean was kissing him. Dean Winchester was kissing him. This was too bizarre for words. Castiel could feel Dean's tongue against his lips and he quickly parted his mouth more out of shock than anything else. Ok he wasn't going to lie, Dean was a damn good kisser but he was also Dean Winchester, Hollywood actor and the object of lust for nearly every woman in America.

The object of lust for every woman in America now had his tongue and Castiel's mouth. Oh and his hands had begun to grip at Castiel's messy hair making it took even scruffier than it normally. Not that Castiel cared, Dean Winchester's tongue was in his mouth why should he care about anything else?

But then he thought that this wasn't fair at all. It wasn't fair to Castiel at all. Dean was...well Dean was straight! He was the poster boy for America, he couldn't be...holy shit, he couldn't be sliding on hand down the back of Castiel's neck and gently starting to bite Castiel's lower lip except he was... Everything inside of Castiel's head was telling him to stop kissing Dean back but his body wouldn't agree at all. He carried on kissing Dean back with as much force as Dean was giving him. The feeling inside of his chest was that of a force of nature, a monstrous hurricane swelling inside of him and threatening to consume him in all entirety. A fire was overwhelming his body and he begged, almost prayed, for Dean to never let him go or him to never stop kissing him.

"I've…I've been thinking 'bout this since the other night in New York…before even…" Dean said between frantic kisses. Castiel looked at him for a moment and saw the sincerity in his words. Those two days with Dean when Castiel had been thinking of nothing else but Dean and now…now he had found out that Dean had been thinking of him. When Castiel thought that Dean was thinking of Anna he was actually thinking of Castiel... Castiel's heart hammered against his chest and because he was terrified of saying something wrong he just pulled Dean into another furious kiss. Dean's hands were at Castiel's waist, gripping the ends of Castiel's shirt and making Castiel's chest tighten even more. His breath became ragged with every deepening kiss. "Cas..." Dean sighed deeply pulling away from Castiel and the fire in Dean's green eyes was so fierce that it almost scared Castiel. This wasn't just a whim of Dean's this was serious and Castiel could easily ruin the whole moment by saying or doing something wrong. Castiel doubted he would ever get this chance against though and he needed to take it.

"Bedroom." He practically moaned as he began to guide Dean to his bedroom with desperate kisses full of teeth and tongue. As soon as they were inside Castiel's bedroom he kicked the door closed and pulled Dean into yet another kiss. The feel of Dean's lips against his own was addictive, it was a drug that was steadily working its way into his blood stream and completely intoxicating him.

Their hips rutted against each other and Castiel's pulse quickened frantically. Dean's lips moved from Castiel's mouth to his jaw and Castiel couldn't help but let out a low moan. He needed to get out of his shirt; he had to feel his skin against Dean's as soon as possible. Castiel quickly unbuttoned his soft and worn shirt throwing it somewhere in the room, he didn't really care where. Dean let out a low chuckle which Castiel had to admit was ridiculously hot. Now that he was here Castiel knew he never wanted to go back to how he was before. He never wanted to go back to the tentative friendship he and Dean had been building since they had first met. True he still thought Dean was a shitty actor who had made some terrible films but it was hard to hate a guy that was slowly kissing your neck and whose hips were rutting against your own.

Without even realising have was doing Castiel gripped at Dean's hair as he wrapped his legs around Dean's waist. Dean emitted another chuckle as their mouths met again even more uncontrollably than before. The kisses were wet, deep and they made Castiel's skin blaze with something he had never felt for anyone before.

Dean pulled away and for a brief moment Castiel thought that he'd change his mind until he realised that Dean was removing his own shirt. When he saw Dean tanned and incredibly toned chest Castiel knew there was no possible way to hide the erection in his jeans. Dean clearly knew the effect he has on people, Castiel could tell from the look on his face and when Dean's hand travelled along Castiel's chest towards Castiel's crotch the smile on Dean's face was electric. It was full of mischief and happiness, desire and sincerity; Castiel couldn't help but tightening his grip around Dean's waist and rutting his hips even more. Dean gave him a wink and Castiel knew what was coming next.

That's when the front door to the apartment slammed loudly. A shock of something, almost like electricity ran through Castiel's skin as he heard footsteps.

"Fuck." Castiel hissed detaching his legs from Dean's waist and thinking of the least sexy thing possible to get rid of his erection. It was kind of of difficult when Dean was still shirtless.

"Yo Cassie! You in?" Someone called out. Gabriel. Of all the people in the world it _had_ to be Gabriel didn't it?

"Fucking _hell_." Castiel muttered grabbing the nearest shirt and quickly buttoning it up. "I'll be right back." He whispered to Dean whose face was a mixture of shock and worry. Castiel hoped it was because of Gabriel being here and not what they had just been doing. Castiel hurried out his room and frowned when he saw Gabriel looking through the fridge.

"Seriously there is nothing in here but take-out and juice. You and Anna seriously need to learn how to fucking cook already." Gabriel muttered.

"For fuck sake Gabriel! What the hell are you doing here?" Castiel asked. "I thought you went with Anna to Ruby's party."

"I only went to try it with Ruby and she was kissing this tool of an asshole after about half an hour so I cut my losses and came back here." Gabriel said shrugging his shoulders as he rooted through the fridge. He looked over towards Castiel then stopped "Wait, why do you look so out of breath? Have you got sex hair? Wait…is your shirt on inside out? You weren't hooking up with anyone were you?" Gabriel asked suddenly looking very interested in Castiel's state. "You were about to have sex, weren't you? Who with?"

"Gabriel…please _leave_." Castiel snapped because he did not have the patience right now to be remotely pleasant towards Gabriel.

"You _were _about to have sex! Way to go Cassie!" Gabriel said chortling.

"Fucking hell Gabriel, can you get out of here please?" Castiel asked making sure Gabriel could hear how annoyed he was while still saying the word 'please'. Gabriel looked at Castiel and he could probably see the anger that Castiel was radiating because he held his hands up in mock defeat.

"Whoa you're pissy when you're trying to get laid. Fine, fine I'll go so you can go and enjoy your sex though it better not be with that asshole pseudo-genius you were in love with. I'll go back to Ruby's and try it on with some drunken college chick." Gabriel said sounding frustrated, not that Castiel cared at all.

"Yeah you go and do that Gabriel." Castiel muttered glaring at his brother. Gabriel gave Castiel a lecherous smirk as he opened the door.

"Don't forget to be safe dear brother." Gabriel said and before Castiel could say anything else, or throw something at Gabriel's head, he swiftly shut the door. Castiel groaned loudly and with a reeling head he went back to his room where Dean was still sat on the bed. Still shirtless.

"Well that was close." Dean said with a slight smirk.

"_Goddamn_ Gabriel." Castiel muttered with annoyance. Before Gabriel had turned up Castiel had been in the middle of something that made him truly happy, being with Dean had made him very happy yet now that he was back in his room, now that he was looking at Dean on the other side of what had happen he was now doubting himself. Dean had said he'd been thinking about kissing Castiel since New York but what if it was just an itch that needed to be scratched? What if Dean wanted to experience something new just for the hell of it? Castiel couldn't risk that.

"Has Gabriel gone?" Dean asked.

"Yeah...it's a good thing he came here actually...he stopped whatever might have happened." Castiel said and he saw Dean's face harden with frown.

"Seriously Cas? What the fuck do you mean by that?" Dean asked pushing himself off the bed and striding over to Castiel. Castiel really wished he would put his shirt back on because it was getting difficult to concentrate with that much toned, tanned flesh within his grasp.

"It means...what is this Dean? Am I just some itch or something like that?" Castiel asked because he was seriously wondering what the hell was going with he and Dean right about now.

"What the fuck Cas? Just some itch?" Dean asked sounding very annoyed.

"Yes. Some itch that you feel that you need to scratch and once that's over you go back to your humble apple pie life...though the apple pie will probably come from some overpriced Manhattan bakery." Castiel said trying to look anywhere but Dean's chest. Sadly he chose Dean's eyes which were just as bad when it came to their absorbing nature.

"Fucking hell Cas...that's what you think this is? Do you think that this is just some impulse that I've decided to act on all of a sudden?" Dean asked.

"Isn't it?" Castiel retorted because this was a thought that was slowly creeping into Castiel's mind.

"No it fucking well isn't!" Dean yelled getting very close to Castiel's face. If Castiel moved just a centimetre closer to Dean they would be kissing again. "God...is that what you really think of me?" Dean asked looking more hurt than Castiel had seen him since they had met. Castiel could make countless jokes about Dean's films towards him but once Castiel had questioned why he was here, why he was here with Castiel more importantly, the hurt was so evident.

"I don't know what to think if I'm being perfectly honest Dean." Castiel admitted.

"This isn't just some itch Cas, if anything the other times were itches..." Dean muttered.

"What?" Castiel asked.

"The reason I was made to do the 'Win A Date' competition, it wasn't because I wanted good publicity or a chance to get closer to my fans. It was damage control my agent forced me into after some sleazy photographer got this photo of me in Greenwich at this party."

"Is Greenwich that bad of a place that a photo of you there could ruin your career?" Castiel asked and he felt a lot better when Dean smirked.

"No I think it was more to do with the fact that I was getting my dick sucked by a guy." Dean said and Castiel choked out a gasp. "Yeah so this, it isn't just some itch I'm trying to scratch Cas." Dean said looking at Castiel searchingly.

"Are you sure?" Castiel asked. Instead of answering him Dean just pulled Castiel into a kiss that caused the fire inside of Castiel to ignite again.

"I'm sure Cas. I've never been surer of anything in my life actually." Dean said once he's pulled away from Castiel. "I wouldn't be here if I wasn't absolutely sure." Dean's voice was strong, unwavering and full of honesty Castiel could hear despite his belief that this could still go wrong for him. Dean's grip on Castiel was firm and warm, it made Castiel feel that Dean really was being truthful. "Now, where were we before Gabriel interrupted?" Dean asked with a slow and lazy smile that Castiel had seen in countless films. Castiel couldn't help but smile back and lead Dean back towards his bed. There was nothing stopping him now, Dean's honesty had melted away some of his fear, and Castiel longed for nothing more than to feel all of Dean's skin against his. He wanted the heat, the closeness and the whole intimacy of it.

Holding onto Dean's wrists Castiel pulled him into a deep kiss, full of longing and biting of lower lips. He could feel Dean's pulse quickening and that sent slivers of joy through Castiel's body. Dean wasn't just here because of some random urge, he was here because he wanted to be with Castiel…Castiel was wanted. Moving his hands from Dean's wrists Castiel ran a hand along the top Dean's jeans that were resting on his hips. With a smirking smile Castiel quickly unzipped Dean's jeans and chuckled slightly as Dean wriggled out of them until he was just in his snug looking boxers. He was so perfect that Castiel couldn't help but pull him into a kiss. Adding intensity to the kiss Castiel pushed Dean slightly until Dean's legs hit the end of the bed. Castiel couldn't stop a laugh from escaping his throat.

"Oh, you think that's funny?" Dean asked pulling away from Castiel for a moment and raising an eyebrow.

"Yes I do actually." Castiel said lowering his voice to what he hoped was a seductive level. From the way Dean smirked at him it worked. Taking charge again Castiel pushed Dean even more so causing Dean to fall back onto the bed. Once again Castiel chuckled while Dean looked incredibly amused. Lowering himself down until his thighs were either side of Dean's waist Castiel leaned in for yet another kiss because Dean's kisses were fucking addictive. "Have you ever-"

"No…" Dean said suddenly looking slightly freaked out.

"If you want to just leave and forget this whole thing happened then you still have that option." Castiel said but he tightened his grip on Dean's waist making it clear that Dean was going nowhere.

"Don't be a fucking moron Cas." Dean said rolling his eyes. Castiel smirked and leaned in to kiss Dean along his jaw. He heard Dean let out a moan which thrilled Castiel. Castiel feathered kisses along Dean's jawline and down his neck until he reached Dean's collarbone. "God Cas…" Dean murmured. Castiel had been waiting so long to taste Dean's skin, how that it was happening he wouldn't believe it at all. He wanted to taste every part of, he Dean wanted every part of Dean and never wanted Dean to leave him.

He never wanted Dean to leave him and that notion rocked Castiel to the core. Pulling away from Dean for a moment Castiel stared down at him. He never wanted Dean to leave but it was going to happen no matter what happened between them.

"What is it?" Dean asked Castiel looking up at him questioningly.

"Nothing…it's nothing." Castiel said leaning in and kissing Dean fiercely. The remaining clothes were soon pulled off until there was nothing but warm skin against skin, hands roaming along arms, legs and chest.

Castiel wasn't even sure whose breathing was more ragged as they rutted together, Castiel's legs firmly around Dean and their kisses changing from kisses to just heavy breathing and the biting of lips. Castiel's skin was burning, the hurricane in his chest threatening to engulf him in all entirety but he didn't care because he was here with Dean and for these moments Dean wasn't going anywhere. Dean broke away and rested his head against Castiel's chest for a moment before breathing out heavily. He moved away slightly and looked up at Castiel with a determined look in his eyes and Castiel couldn't help but smirk. There was no way he was ever going to let Dean out of his life now that he was here, no way. He'd spent too long pretending that this wasn't what he wanted, too long pretending that Dean wasn't the one he wanted but he was determined to never do that again.

* * *

Castiel's mind was hazy but it was the pleasurable haze that made him happier than anything else in the world. Dean was lying next to him just breathing in and out with a contented smile on his lips. An arm rested across Castiel's waist, the warmth of it seeping into his skin as Dean's smile broadened. Looking up into Dean's eyes Castiel couldn't help but lean forward until their lips met. What started as a light kiss ended up deepening until Castiel could feel the pull of longing in his stomach. Dean's teeth nicked at his bottom lip and as he let out a small moan he could feel the rumble of a laugh deep in Dean's chest. Just the sound and feel of it was enough to make Castiel fall for Dean even more than he could feel himself already falling. There would be a time, no doubt in the morning, when Castiel would begin to worry but for now he was just going to sink, care about nothing other than being here with Dean in the moment.

He watched as Dean slowly glanced around his room taking in the stacks of books, CD cases littering the desk he used as a bookcase/place to throw things onto than an actual desk and random items of clothing that had been chucked haphazardly onto the desk's chair. Having Dean Winchester not only in his room but only naked in his bed should have sent Castiel into a spin of nerves and worry but he was too tired, too in awe that he was wanted by Dean, to actually care that there was another person in his room and taking in all the things that made him _Castiel_.

"Hey, is this your mom?" Dean asked leaning over slightly to pick up the small photo frame on Castiel's bedside table that showed a woman with Castiel and Anna at the age of four. Castiel looked at his mother's face and could easily pick out bits and pieces of himself and Anna in her features. Anna had inherited her dark red hair but Castiel had her bright blue eyes and full lips. Castiel's heart beat painfully in his chest when he thought of his mother but he tried not to let it show.

"Yeah, that was taken a week after we moved. She spent two whole days painting the rooms that Anna and I claimed as ours. Mine was green and Anna's was purple. I had matching bed sheets and everything." Castiel said remembering the joy he had felt at the age of four seeing his new bedroom for the very first time. He remembered the look on his mother's face and how wide her smile was because she knew that she had brought joy into Castiel's life.

"What happened to her?" Dean asked gently as he reached over towards Castiel and ran a hand down his side. Castiel felt a shiver of pleasure run down his side and he moved slightly closer towards Dean as he glanced at the photo that Dean was looking at.

"What do you mean?"

"Well…you've never spoken of her until now and there are hardly any photos of her in your apartment…." Dean said.

"She…she died…giving birth to Gabriel. She had this heart condition…it was a defect from birth, my Uncle Michael has it as well but not as serious, and Gabriel's birth was too much for her…she died from a heart attack. After her death my Uncle Michael took us in. Anna and I lived with him and my Aunt Rachel until we moved here for college. Gabriel still lives with them though back in Lincoln. The house we went to pick up Gabriel from is theirs." Castiel explained in a small voice.

"What about your dad?" Dean asked.

"Anna never told you any of this?" Castiel couldn't help but ask because Castiel honestly thought that Anna might have told Dean about this.

"No, she only ever talked about you and Gabriel. It seemed like a really personal subject and Anna didn't seem to want to talk about." Dean said with a vague shrug. Castiel couldn't blame Anna for not talking about this to be honest; she never really liked talking about their parents and always preferred talking about her brothers whenever people asked her about family.

"Yeah…Anna…Anna never talks about our father. He…well he left us when our mother was pregnant with Gabriel. I haven't seen him since I was five years old." Castiel explained. "He was never really around when we were growing up anyway so it wasn't that much of a shock when he did walk out on us but it still hurt like hell thinking about how our father just up and walked out on us." He tried to keep his voice steady at this but talking about his father had always been a sore spot for Castiel. As far as he was concerned his Uncle had done the best job anyone could do at raising him, he never needed a father when he had his Uncle.

"You could still find him and he could make things up to you." Dean said gently as his fingers snaked down Castiel's arm sending shivers down his spine.

"I doubt that Dean; he died when I was thirteen, he was in a car accident in Minnesota and died a few days later in hospital. I didn't find this out until three years later though. I tried to find him you see and after nearly four months I did indeed find him, well his grave...Anna and Gabriel have no idea and when I told Uncle Michael he agreed with me that I shouldn't tell them. Anna's never really wanted to know about him and really resented him for walking out on us; Gabriel's never met him and I don't think he ever had any intention of getting in contact with him." Castiel said in a small. He had never told anyone this in his life. This was his secret and to finally be telling someone, Dean of all people as well, was strangely freeing.

"Fuck…I'm sorry Cas…if…if it's any consolation I know how you feel…my mom died when younger then my dad was killed when I was eleven. Jo's mom Ellen pretty much raised my brother and me along with my dad's best friend Bobby." Dean said pulling Castiel closer to him and placing a soft kiss on Castiel's forehead. Everything felt so natural with Dean, like Castiel had been inadvertently waiting for this since before he had even met Dean, before Dean even knew he existed. "I guess we're just two sides of the same 'orphaned, relying on relatives, sibling loving' coin huh?" Dean asked.

"Yes, I guess you could say that…" Castiel mused before Dean pulled him into a deep kiss. "I…I never knew about your parents…you've never spoken about them before have you?"

"Not to the press, no." Dean said quietly. "It's my life…my past and the press…I feel they have no right to know about my past. I'm not ashamed at all, I mean Ellen and Bobby raised Sam and I and they did a damn good job and they tried to make Sam and I people that we weren't. The press wouldn't really care about that, they would only care that my parents had died leaving 'the poor Winchesters alone in the world' when that's complete bullshit. I was never alone. I always had Sammy, I had Jo and I had Ellen and Bobby." Dean said. Castiel understood now why the Dean that he saw on television was so different from the Dean he was leaning against. That Dean, the Dean seen on countless interviews and on the red carpet, was just façade created so the real Dean, the Dean that was with Castiel now, didn't have to show the world his family life and didn't have to be judged for anything. Realising that he was probably one of the first people hearing Dean talk like this made Castiel smile slightly. Dean was being completely honest with him, completely open with him and just thinking that made Castiel smile slightly.

"Thank you." He said reaching up and kissing Dean softly.

"What for?" Dean asked.

"For telling me that, it clearly meant for you to say that so…so thank you." Castiel said. Instead of saying anything Dean just smiled and rested his head on top of Castiel's. It was comfortable and Castiel had to admit that he could have easily stayed like that forever.

* * *

Castiel was vaguely aware of movement and he opened an eye blearily. He so rarely got to lie in and he had been looking forward to one until he felt himself being awoken. Looking across the bed he noticed Dean sitting up and combing his hair with his fingers.

"Dean?" Castiel asked with a voice croaky from sleep. Dean turned his head slightly and gave Castiel a quick smile.

"Sorry, I woke you up didn't I?" Dean asked.

"It's fine." Castiel mumbled moving across the bed until he was behind Dean. He placed a light feather kiss on Dean's neck until he reached Dean's strong jaw.

"That's very distracting, I hope you know that." Dean said between light chuckles.

"That is the point Dean." Castiel said between kisses along Dean's jaw. Slowly he wrapped his arms around Dean's waist and held on tightly.

"_Cas_." Dean moaned and Castiel couldn't help but snicker. "You're evil Cas. I need to get going before Jo thinks I've been murdered or run off to join the circus and you're making it very difficult to want to leave."

"Do you have to go?"

"Yeah, plus I'd rather not be here when your charming brother returns." Dean said.

"You have a point there." Castiel sighed as he detached his arms from Dean's waist so Dean could put his shirt back on. Castiel was very smug when he noticed that there was a love bite on Dean's collar that couldn't be hidden by his shirt. Dean noticed this and raised his eyes at Castiel. Castiel shrugged his shoulders while smirking and Dean simply rolled his eyes as he got dressed. Castiel reached towards the nearest small pile of relatively clean clothing and picked up a pair of sweatpants. Despite it being very tempting Castiel resisted dragging Dean back down onto the bed and followed him out of the bedroom instead. It should have awkward between them after everything that had happened during the evening but it didn't and that made Castiel slightly sure that this was a good thing, that this was the right thing.

"I have missed calls from Pamela so no doubt I'll have crap to sort out later on but after that we could go and grab a drink…or something…" Dean said sounding slightly nervous which made Castiel smile.

"That sounds good to me" Castiel said before Dean pulled him into another kiss. "If you carry on doing that I'm going to drag back into my room." Castiel said as Dean kissed along his jaw.

"That's tempting but I really do have to go." Dean said. "I'll see you later then?"

"Yeah…see you." Castiel said with a slight smile before Dean walked out of the apartment. Castiel sighed for a moment before checking the clock hanging above the television. It was eight o'clock in the morning so there was no possible chance of Anna or Gabriel coming home anytime soon. He should have gone for a shower, after all Gabriel would only make some smartass comment about how Castiel smelt like sex but just a few moments he wanted to smell Dean on his skin before he went to shower.

* * *

Anna and Gabriel came home, looking slightly worse for wear, as Castiel was making himself breakfast. Even before he took a good look at Anna he knew that she would need copious amounts of coffee, Pop Tarts and maybe Jelly Beans.

"How much does your head hurt?" Castiel asked as Anna gently placed herself onto the couch and groaned loudly.

"Ruby made cocktails so does that answer your question?"

"Pretty much" Castiel said. Ruby's cocktails were pretty much poisonous and even smelling them would comatose you. "Here, this should help" Castiel said handing Anna a mug of coffee.

"Thank you…now if the room would stop spinning the world would be a better help." Anna muttered.

"What, you're not going to make me any coffee?" Gabriel asked. Castiel raised an eyebrow.

"No I'm not." Castiel said with a smirk. Gabriel rolled his eyes and stomped over to the kitchen to get his own coffee. Well that's what he got for barging in last night.

"So Cassie…how was the sex last night?" Gabriel asked crudely as he poured himself a generous mug of coffee. Castiel narrowed his eyes at him and turned away because he really didn't want to talk about his night with Dean to Gabriel of all people.

"What is he talking about Castiel?" Anna asked with a questioning look as she pulled herself off the couch and walked slowly into the kitchen.

"Cassie got laid last night" Gabriel said bluntly.

"Gabriel!" Castiel snapped while Anna's eyes widened in surprise as she grabbed the box of Pop Tarts. "Christ!" Castiel then muttered under his breath. Sometimes he really hated his brother.

"What? Who was it? Wait…how does Gabriel know?" Anna asked sounding hurt after all Anna was the one that knew most things about Castiel not Gabriel.

"Remember when I left Ruby's? I came back here and-"

"Please let this not be a 'Gabriel walked in and saw you having steamy sex on the couch' story." Anna said pleadingly to Castiel.

"No it is not one of those stories. Besides I would never have sex on the couch, we eat on that couch." Castiel said rolling his eyes.

"I've had sex on that couch." Gabriel said with a nonchalant shrug.

"Gabriel! That is gross" Anna snapped whacking Gabriel across the back of the head.

"Not really, it was damn kinky though. She was a _very_ flexible freshman taking a course in interpretive dance." Gabriel said with a wink.

"Oh God, I don't want to hear any more of your sexual adventures on our couch thank you." Anna said glaring slightly at Gabriel "Now tell me, what happened last night?" She added beseechingly.

"Well I came home and Castiel has some very convincing sex hair then he swiftly kicked me out so he could go back and have sex."

"With who?" Anna asked Castiel. God he hated lying to Anna but how could he say that the person he'd had sex with the night before was Dean of all people. "Castiel?"

"I…I…" Castiel mumbled looking into Anna's face and hating the look that she was giving him because he couldn't lie to her, he just couldn't.

"Gabriel, I think we're out of Pop Tarts. Can you go and grab some?" Anna asked placing the box of Pop Tarts back on the counter. Castiel knew for a fact that this was a lie because the box was actually full but Anna was clearly trying to get Gabriel out of the apartment.

"But I want to-"

"Gabriel, go and get some Pop Tarts." Anna snapped walking over to Gabriel and thrusting a handful of dollars into his hand. " Now." She added firmly. Gabriel sighed loudly and Castiel could hear him muttering under his breath as he stomped out the apartment. Once the door closed behind him Castiel sighed loudly.

"Thank you" He said to Anna.

"It was Dean, wasn't it?" Anna asked unable to keep a smile off her lips.

"Wait…how…how did you-" Castiel stuttered.

"When I told him that nothing was going to happen between us I gave him several reasons…one of those reasons was because I knew he wasn't as into to me as he was trying to convince himself that he was. I knew that…I knew that he liked someone else and that someone else clearly liked him…"

"Anna-"

"I'm not remotely angry at you Castiel if that's why you're worried. I knew from the way you looked at one another, I knew it as soon as you came back from New York. You…you gravitated towards one another and I knew that things had changed." Anna said. "I…I like the Dean that drove for over twelve hours to come to Chicago, the Dean that cooked for us and actually got on with you but…but you…I think you love him, it's clear to see."

"He's going to leave though. He's going to leave in a few days and go back to New York. He's _Dean Winchester_, he's one of the most famous people in America and I'm in love with him…"

"Well at least you're admitting it. I thought it would take you a millennium to admit it."

"Admitting that I might love him isn't the problem here Anna, the problem is that I'm going to still love him even when he leaves me here." Castiel said. Anna sighed for a moment before she pulled Castiel into to firm hug.

"Maybe you should just wait to see what happens Castiel, if you spend too much time worrying about everything then you'll never be able to truly appreciate what is right in front of you." Anna said.

"When did you get so smart?" Castiel asked.

"Oh me? I've always been this smart; you've just never come to be for relationship advice before." Anna said smiling. "Now stop worrying and…and just live because if you screw this up then you're going to regret it…and I might go insane." Anna said and in that moment Castiel really did love his sister and just how much of a good person she was.

* * *

**Author's Note: I really hope that none of you were praying for this chapter in which Dean and Cas have sex because I am a fucking awful smut/romance writer so instead I just wrote Interupting!Gabriel, lip biting and forehead kissing because I love lip biting and forehead kissing in fics. **


	13. Chapter Thirteen

**Chapter Thirteen**

Jo loved motels, she always had. Even when Dean had offered to pay for expensive hotels for them to stay in if they had gone anywhere Jo had turned down that offer in favour of saying in some crappy motel with bad TV reception and suspicious looking towels. Apparently it reminded her of all the road trips they had taken as kids with Bobby or Ellen, they reminded her of the times that she and Dean would stay up late with Sam eating junk food from the vending machines and watching whatever bad horror films were playing on the motel TV. Sam would always go to sleep quickly because he'd get scared but Dean and Jo would stay up for hours laughing at the fake blood and throwing M&Ms at one another. Now it was more Dean and Jo sat watching bad films with beer though the junk food from the vending machines was still a necessity. Jo's love for motels and the memories that came with it were just some of the few things that made Dean really love Jo sometimes.

When Dean returned from Castiel's, tired but happier than he had felt in a long time, Jo was fast asleep on her bed and snoring slightly. She was lying like a starfish with her mouth wide open and half her face smashed against her pillow. She looked peaceful and it seemed that there was no waking her, not that Dean wanted to do that any time soon, and so Dean decided to go for a shower.

As the hot water hit Dean's back he was hit with the memories from the night before. After weeks of thinking that Castiel only thought of him as a complete asshole the knowledge that Castiel didn't think of him as an asshole but also might have been in love him was a lot to think about. It was an awful lot to think about. Not only had someone said that they loved him but it had been Castiel of all people, sarcastic and smart Castiel.

Now the main problem was Pamela who had spent so much time trying to hide part of Dean from the world. There was no possible way Dean was going to tell Pamela yet because it would actually ruin everything once Pamela told him just how against she would be when it came to Dean having a relationship with Castiel. Pamela had been in control of Dean's public and private life for so long but now…now Dean wanted to be in control of this because he really did care for Castiel. He cared about Castiel and he needed him. Dean needed Castiel and that thought, that realisation was so surprising to Dean and that made him understand just how much he had grown to care for, and possibly love, Castiel since they had met.

* * *

Jo was awake when Dean came out of the shower though by the look of the huge pillow indentation on her face she hadn't been awake for long. Jo yawned loudly and stretched out like a cat before grinning up at Dean with a lascivious smirk on her lips.

"What happened to you last night?" Jo asked still smirking. "I was going to text you to see if you wanted to hit some of the bars here because apparently Chicago has some good bars according to some of my friends back in New York but you said something about talking to Anna so I decided to just leave you to it. I stayed here with a huge bag of Resse's Piece and was very happy because there was a very fascinating documentary on last night about the rise and fall of the Roman Empire; it was both exceptionally bloody and highly informative."

"You've been spending far too much time with Sam if you find a documentary on the rise and fall of the Roman empire fascinating." Dean muttered rolling his eyes at Jo.

"Shut up Winchester, it was brilliant." Jo said.

"You're a closet nerd." Dean said shaking his head.

"And you're dodging the question. So where were you?" Jo asked.

"I…I was at Cas and Anna's apartment."

"Oh yeah? Wait…did you talk to Anna about the thing? The last thing I heard was that you were going to go coffee with heard then you went MIA on me. Did you talk to her? Did you talk about the thing?" Jo asked.

"Yeah…yeah I did." Dean said as he shrugged his shoulders slightly.

"And…what did she say? God, trying to get a coherent conversation out of you is like trying to get blood out of a stone." Jo groaned loudly.

"She basically said that it would be better with us being friends as she didn't want to be flung into the limelight even more so than she has been already." Dean said scratching his neck somewhat. Jo rolled her eyes again which didn't help at all really. "What?"

"You said you told her about the thing…so tell me what she said when you told her about the thing."

"Ok…I didn't tell her about the thing." Dean said.

"For fuck sake Dean! I actually despise you sometimes." Jo snapped. "Why didn't you tell Anna about how you felt about Cas? She could have helped you know?"

"Jo, I didn't need to tell her because I think she already knew. She said some stuff that made it clear that she thought there was something between Cas and I…Jesus I sound like such a damn girl. Christ…" Dean muttered as he pulled a shirt on over his t-shirt. Jo rubbed her face trying to get rid of the pillow indentation though it did nothing to help in the end.

"Glad to know that Anna has eyes and isn't completely blind." Jo said sounding slightly muffled as she continued to rub her face. "What happened after that? You know, after Anna pointed out that it's obvious you're into her brother" Jo added once she stopped rubbing her face and stretched out again.

"We talked…"

"You talked…fantastic…did anything happen after you talked?"

"Well Anna left the café and that gave me some time to think."

"Well there's a first for everything in life I guess." Jo said with a smirk. "Then what happened? Please just tell me before I go insane."

"I ended up at Cas' apartment. We talked… well we kind of yelled at one another then I kissed Cas-"

"Wait…you kissed Cas and that wasn't the first thing you told me about? Dean your priorities are fucking awful!" Jo said groaning loudly as she crashed back onto her back.

"Yeah…Cas and I kissed…"

"And?" Jo asked from where she lying on her bed.

"And what?" Dean said with a shrug.

"You're being cagey…and you're only cagey when something big went down." Jo said suddenly sitting up quickly and staring up at Dean "Holy shit! You did more than kiss didn't you?" she then asked between pearls of laughter.

"Jo-"

"Holy shit…you and Cas had sex didn't you?"

"Jo-"

"You had sex with Cas! Oh my God, I am so damn proud of you right now."

"Thanks Jo. As you know I spend all my time seeking your respect." Dean said sarcastically as he rolled his eyes.

"Oh stop being pissy with me Winchester, you got laid last night and with someone you clearly like so I'm going to sit here and be damn smug about it because I was right when I said that Cas would be butt naked screaming your name before the month was out. I feel like a proud mama bear right now." Jo said. "Wait is it's appropriate for a mama bear to be proud of hot steamy sex?" Jo then asked frowning slightly.

"How do you know it was hot and steamy?" Dean asked.

"Cas looks like the kind of guy." Jo said with a shrug. "So getting back to the important and serious bullshit…what are you going to do? About Cas I mean…you clearly like him _a lot_ and he's obviously crazy about you despite him being a much better than you."

"Jo-"

"He's smarter than you and never starred in a Doritos commercial playing air guitar to ACDC." Jo said. Dean winced slightly at the memory of that damn commercial which Jo and Sam had mocked him about for months after it started airing. Damn Pamela…

"Where are you going with this exactly? And I don't mean about the Doritos commercial, I mean about Cas." Dean asked because Jo's constant questioning was starting to get to him. He had not slept enough last night, he hadn't had enough coffee and he was damn tired. He was tired but happy and Jo's constant questioning was making him lose the happy feeling in his stomach that he got whenever he thought about the night before with Cas.

"What I mean here is that you better tell me that you're not going to throw it all away with Cas because Pamela is going to have a fit once she has to tell the press that you're dating a guy."

"Who says I'm going to tell Pamela this?" Dean asked. "And who's to say that I'm going to date Cas?" Dean added even though there was no way that he was going to lose Castiel now that he had found him. Dean might have done some stupid stuff in his life, like thinking it was a good idea to once attempt a backflip off a diving board when drunk thus resulting in two chipped teeth, but he wasn't going to do another stupid thing like let Castiel go.

"For fuck sake...don't be so stupid. Pamela knows everything about you Dean, she knows about the cow tipping incident, she knows about the time when we were fifteen and you got arrested to smart talking a cop and she even knows about the time you got suspended for punching that guy who pushed Sammy down the stairs in high school. She is going to know about this and she's going to freak out because that is the only thing that Pamela ever does. She freaks out when she thinks that your precious image is at stake so she is going to freak out when she finds that not only are you going to date someone but the someone that you are going to date is the brother of the 'Win A Date' girl. She is going to freak. Simply as."

"Yes but if I don't tell Pamela-"

"She'll still find out because Pamela knows everything. She's like some God…or freakishly and accurately psychic." Jo said rolling her eyes heavily "Now what are you going to do when Pamela finds out?" she then asked.

"But if I don't tell her-"

"Dean! Did you not hear the 'God or psychic' comment? Pamela is going to find out, now what are you going to say to her when she does find out?" Jo asked.

"Um…" Dean muttered which made Jo lend forward and hit Dean around the back of his head. "Ow!"

"No Dean, you are not going to say 'Um' because that will give Pamela the chance to yell at you and she _will_ take that chance because Pamela_loves_ to yell at you. You are going to tell her that you don't give a flying fuck that she probably doesn't agree with who you want to date because you are a grown ass man who can make his own damn decisions. You're twenty-six years old Dean and you can make your own fucking choices in life that aren't decided for you by Pamela bloody Barnes!" Jo said breathing heavily with what sounded like relief.

"How long have you wanted to say that to me?" Dean asked.

"For about three and a half years so you have no idea how damn relieved I am to finally be saying all this to you." Jo said groaning loudly. "You're my best friend Dean, we've known each other all our lives and I have never seen you so happy as you were when Cas was in New York with us. I've never seen you so happy than you are right now. Now if you fuck this up then I will kill you because you're clearly into Cas otherwise you wouldn't have had sex with him and I can't remember the last time you actually liked someone enough to actually admit it to them so _please_ promise me that you will not fuck this up." Jo said sighing loudly once again.

"Are you done?" Dean asked when Jo sat back down on her bed.

"Yes but only because I'm hungry and by that I mean you're taking me out for breakfast because this place does not serve waffles so it's getting a firm six out of ten stars from Jo Harvelle."

"You spend far too much time in motels." Dean muttered shaking his head at Jo. "If I take you out for waffles then will you stop talking about this for a while?" Dean then asked. Jo nodded happily with a highly self-satisfied expression.

"Yes…but only until I've stopped eating waffles." Jo then said shrugging.

"Fine I'll take that. Go and get dressed then I'll buy you breakfast." Dean said with a sigh as Jo smiled smugly. Dean rolled his eyes while Jo actually sauntered towards the bathroom to get dressed.

* * *

Gabriel returned to the apartment with a brand new box of Pop Tarts, Apple Strudel because clearly he was trying to get Castiel to tell him things by purchasing Castiel's favourite flavour, while Castiel was explaining the previous night to Anna. Gabriel practically leapt through the door dramatically before taking two steps into the apartment, tripping over the large rug across the floor and Castiel and Anna watched as he crashed to the floor with a loud thump.

"I'm ok." Gabriel mumbled as his face was pressed against the floor. It looked painful yet neither Anna or Castiel moved to help him because Gabriel injured himself more often than a seventeen year old should.

"No one was asking to be honest." Anna said shrugging.

"Both of you are heartless and I demand new siblings." Gabriel muttered from the floor as he held up the box of Pop Tarts. "I travelled all the way to get Pop Tarts, Apple Strudel flavour I might add, and this is the thanks I get."

"The store is a five minute walk away from this building…and you've been gone for over half an hour." Anna said. Gabriel grumbled loudly as he pulled himself up off the floor and threw the box of Pop Tarts onto one of the kitchen counters.

"Yeah well it was obvious that you were kicking me out the apartment so you two could have some twin related bonding time so I gave you that. Plus your store has an excellent candy aisle I might add. Now can I find out about what happened with Cassie last night because I actually really, really want to know?" Gabriel said throwing himself down onto the floor in front of both Anna and Castiel. Castiel glanced at Anna and shrugged his shoulders. "What? Come on, will someone please just tell me what is going on?" Gabriel asked. "I know you two are best friends or crap like that but I'm also your brother and I've been left out of the loop with so much crap recently. Crap like Dean Winchester turning up in Chicago for Anna then Castiel not only being in New York when he's never left the state before a few months ago but driving back to Chicago with Dean Winchester. What is going on?"

"Gabe…I don't really know what's going on at the moment ok?" Castiel said.

"Cassie…Castiel that really doesn't answer anything that I asked. What is going on?" Gabriel said rolling his eyes.

"Gabe look I really…I can't-"

"Ok, Anna, what is going on? Clearly Castiel isn't going to tell me anything so I'm going to ask you." Gabriel said turning away from Castiel to look at Anna. Anna chewed her lip for a moment before sighing loudly.

"I ended things between Dean and I yesterday and one of the reasons was because I knew that Castiel is in love with him."

"Anna!"

"Oh for God's sake Castiel! You told him that you love him and you slept with him last night-"

"Dean Winchester was the one here last night? As in _Dean Winchester_? Dean Winchester has had sex with one of siblings but it was _Castiel_? Wait…Dean Winchester is _gay_?" Gabriel babbled as he stared at Castiel with a shocked expression.

"Gabriel-"

"This…this is huge and I mean _huge_. It's crazy…and it happened to _Castiel_ of all people."

"What is that supposed to mean?"

"You're a sarcastic and boring nerd! When you're not sitting in your room watching some depressing film or reading a book written by a guy that died far too many years ago, whenever you actually do go out you just go to that crappy bar full of pseudo-intellectuals with that lanky Alfie guy who is, not so secretly, in love with Anna."

"Gabriel-"

"Shush I'm actually talking and hoping that someone will listen to me for once. You're a nerd Castiel who doesn't even like _Cupcake Wars_ and the fact that Dean Winchester is into you is just…well its crazy." Gabriel said shaking his head.

"Thanks Gabriel…thanks…though I'll have you know that my dislike for _Cupcake Wars_ is actually a good thing." Castiel said which made Gabriel roll his eyes heavily.

"It's just…you and Dean Winchester…no offence but this is going to take some getting used to." Gabriel said. "I mean…you and _Dean Winchester_. It's like some really cheesy romantic comedy…that Dean Winchester would probably star in to be honest." Gabriel added with an awed look towards Castiel. "You know what Cassie? I am very proud of you right now and I'm actually happy to call you my big brother"

* * *

"So….how was the sex?" Jo asked leaning across the table of the small diner she and Dean were sat in. Every now and then someone would look over as if to wonder if Dean was actually Dean Winchester before turning back. Dean wished that Jo would lower her voice because it was beginning to carry across the diner despite the general noise of orders being taken, coffee being poured and overall chatter.

"Eat your waffles and be quiet Jo." Dean said as he sipped his coffee.

"_Dean_! I haven't had sex in four months, sixteen days and twelve hours so I deserve to know how your sex was last night but not in a graphic way because that would be gross. I don't mean that in the 'you had sex with a guy' gross but the 'you're like my brother and I don't want to hear about my brother graphically having sex' gross" Jo said animatedly.

"You know it's sad when you have an actual countdown from the last time you had sex right?" Dean asked pointedly.

"Shut up about the damn countdown and just tell me about last night!" Jo said rolling her eyes.

"I thought you had sex with that tattoo artist from Brooklyn the other week." Dean said trying to deter Jo.

"Oh God no! He drank too much tequila and passed out on my couch so I rang my mom up and ended up complaining to her for two hours about how there are no decent men to date in New York." Jo said reaching for her own cup of coffee and swiftly draining it.

"It would help if you actually started looking for decent guys and not just hook up with the painfully hip douchebags that frequent your bar."

"You frequent my bar." Jo pointed out.

"Because you work there and they play good music not because I actually like the place Jo." Dean shot back.

"Wait…how did this conversation end up about me and my lack of decent hook ups? I want to know about you and Cas for fuck sake, so just tell me." Jo begged.

"Eat your waffles Jo." Dean said with a sigh.

"I'll eat my waffles when you tell me about you and Cas!" Jo whispered slamming her hands on the table dramatically.

"Fine, I'll tell you about last night if you stop slamming your hands on the table because you're going to cause a scene and the last thing I want is for a scene to be caused in the middle of some random diner in Chicago." Dean said.

"Yay!" Jo said smugly. "Now how did it actually happen?"

"What the sex or the whole thing?" Dean asked

"The whole thing! God…"

"Fine. I went to Cas' apartment to talk to him."

"About bloody time." Jo muttered.

"Are you going interrupt me at every sentence?" Dean asked sighing.

"No, this is the last time. Please continue." Jo said before shovelling a large mouthful of waffle into her mouth and chewing happily.

"Ok so I went to Cas' to talk to him about everything and we sort of got into a fight." Dean said and Jo opened her mouth to say something until Dean gave her a firm glare. She held up her hands in mock defeat and let Dean continue with what he was saying. "So we sort of got into a fight about how Cas constantly went on about how much of a dick I was and it turns out that he was only like that because he was trying to hide the fact that he was into me which really didn't help in the long run because that was one of the damn reasons why I liked him in the first place. I mean, he was sarcastic and blunt and a bit of a dick but that's why I liked him…he's still sarcastic and a bit of a dick but at least now I know that he doesn't think I'm an asshole."

"That's delightful Dean but what happened after Cas explained all of that to you?" Jo asked sounding irritated.

"I thought you weren't going to interrupt again" Dean pointed out.

"You're story is taking a long time. My waffles are going cold here."

"Well shut up and eat them then."

"Fine I will but hurry up with your damn story."

"Fine, Cas told me all this stuff then he gave me this speech about how he chooses not to like people because in then end you just get hurt and stuff like that though it sounded better when Cas said it to be honest then he told me that he liked me, that he might have been in love with me." Dean said and once again Jo opened her mouth to say something but once she saw Dean's face she stopped and just carried on eating her waffles. "Then he just stood there with this sorrowful expression on his face that nearly killed me if I'm being honest and he just begged me to say something…but I couldn't…I just couldn't Jo because he had said all this stuff about why he was the way that he was and I was just so relieved that he didn't hate me and that this _thing_ between us hadn't all been in my head and I just couldn't say a thing." Dean explained with a slight sigh.

"You, Dean Winchester, have no game what so ever." Jo said between mouthfuls of waffle. "And I wasn't interrupting then because that was just an observational statement not an interruption so it was fully justified. Now please tell me that you said _something_ to Cas after he said all of that to you. You couldn't have just sat there and not said anything to him."

"Yeah…well I said 'fuck it'"

"How poetic of you" Jo said.

"Then I kissed him." Dean said and Jo actually pumped her fist into the air. Dean retrained from throwing a bit of waffle at her because of how damn smug she looked.

"Thank God! At least kissing him made up for you saying 'fuck it' of all things." Jo said rolling her eyes. "Honestly after all that romantic crap you have spouted in your films you couldn't have come up with something a bit more quixotic than 'fuck it'?" Jo then asked.

"Cas hates my films, actually he 'tolerated' _The Extraction Point _which is beside the point. The point is that he hates my films so I could hardly quote one of my films in order in to try and convey whatever my thoughts on Cas are."

"Still…'fuck it'…honestly." Jo muttered. "Still…clearly Cas brought it."

"There was nothing to 'buy' Jo ok?"

"So what are you going to do?"

"About?"

"Seriously? God…what are you going to do about you and Cas?"

"I don't know ok? Maybe I should just have a wait and see attitude about it."

"A wait and see attitude? Are you kidding me?"

"No. Look if I go into this whole thing guns blazing then I might fuck it up and…look I like Cas ok and last night was, at the risk of sounding like a woman, actually one of the best nights of my life. Cas and I talked about a lot of things, I mean I talked to him about things that I normally only talk to you or Sam about and that means something ok? I don't want to fuck this whole thing up so if I just wait and see how things go on without freaking out or thinking about it too much then maybe this can work."

"What like you and Cas working out as in being together?"

"Yeah."

"I've got to say that I'm proud of you. I thought you wouldn't do anything about Cas and then I'd have to put up with you being in the most pissed off mood for the next God only knows how many months until you got over it. The fact that you've done something about it makes me pretty damn happy." Jo said with a proud smile. "See? I'm a proud mama bear. Now proud mama bear needs another coffee so scoot." Dean rolled his eyes as Jo grinned happily at him and pulled himself out of his chair to walk up to the counter. Dean was just reaching the counter when he heard his phone begin to ring. He glanced at the screen and saw Pamela's name flash up on the screen. Dean turned back to Jo and mouthed "Pamela" as he held up his phone. Jo grimaced for a moment which wasn't remotely helpful. Dean sighed as he moved out the diner until he was outside.

"Pamela?" Dean asked warily when answering the phone. He wasn't ready for Pamela to yell at him which she was most likely going to do.

"Hello Dean." Pamela said. "I'm not going yell at you so stop sounding so terrified. I'm calling with very good news actually." She added with an oddly cheerful voice. It was even more terrifying than when she yelled.

"Really? You're calling with good news?" Dean asked. Pamela rarely ever called with good news and recently that had certainly been the case so Dean was going to carry on really pretty apprehensive.

"Yes I'm calling with good news. Do you remember that independent film you were being considered for recently?" Pamela asked.

"Yes..."

"Well stop sounding so worried and pissed off because you've got the part." Pamela said.

"I got the role?" Dean asked.

"Yes, yes you got the role. The casting people are really happy that you were interested in the role and they think you can do very good job with it." Pamela said. "So there you go Dean; I'm not calling to yell at you even though I know you're not in New York because I've been calling your apartment since yesterday and there has been no reply. I'm not going to yell at you Dean because I'm over yelling at you." Pamela explained. Pamela never sounded like this so for a moment Dean was tempted to tell her about Castiel but that would easily send Pamela over the edge so he decided against it.

"Well thank you Pamela, thank you."

"You're welcome Dean. I can have a script sent over to your apartment in the week and I'll be hearing more about the role and filming. Just…can you promise me something Dean?"

"Probably not but I'll try."

"Well can you promise, wherever you are, that you won't do anything stupid?"

"Believe me Pamela, this is the first time in my life that I'm not doing something stupid. I'm just doing something for me." Dean explained before saying his goodbyes and hanging up the phone. He then noticed that Jo was staring at him through the diner window like he was a highly interesting TV show. Dean shook his head slightly as he walked back into the diner and sat down opposite Jo.

"Did she yell at you? You didn't look terrified and you're not shaking so clearly she didn't yell that loudly."

"She didn't yell at all."

"Fuck…she didn't yell?" Jo asked and Dean shook his head. "Wow…what did Pamela say?"

"You know that indie film I was looking at recently?"

"Oh yeah, the one that's based on that stupidly depressing book that all the hipsters that frequent my coffee store all seem to be carrying around and crying over?" Jo asked. "What did Pamela say about it?"

"I got the role, the lead role."

"Really? Dude that's awesome!" Jo said grinning widely.

"Yeah, it's a good script and the storyline is actually interesting. It's not cheesy or overly depressing…it feels like the kind of film I actually want to make." Dean said.

"That really is awesome Dean, I know you really wanted that other role but this is just as good right?"

"Yeah, according to Pamela filming starts soon so I guess that's means I'm leaving soon."

"Oh…_oh_. So you have to go and tell Cas that you're leaving…wow…good luck with that." Jo said raising her eyebrows.

"Yeah thanks for that Jo; that really helps." Dean muttered.

"Well I'm always here to help, you know me." Jo said smirking.

"No you're not, you're here to give me snark and for that I'm not going to go and get another coffee now." Dean said.

"You're a real jerk Winchester." Jo said throwing a bit of waffle at Dean.

* * *

Clearly sensing that Castiel needed time to himself to think through what had happened the night before Anna dragged Gabriel out the apartment with the promise of getting him into a nearby bar where there was a strong possibility of Ruby's presence. Gabriel actually waltzed out the apartment like an overstuffed peacock with Anna following behind him while she rolled her eyes though Castiel fully appreciated her kindness.

The silence of the apartment gave Castiel time to think over what he really wanted and what he wanted was Dean. He wanted Dean but Dean would be leaving soon, Dean would be leaving and no matter how much Castiel didn't want him to leave he would be. He could talk to Dean as much as he wanted but it probably wouldn't help in the end.

He needed to talk to Dean, he needed to talk to Dean about this even though it scared him because this was getting dangerously close to the edge of things that Castiel was comfortable with talking about. He had been truthful with Dean the night before about how he chose people to love. He never liked getting close to people because the people that he loved would end up dying. He had loved his mother and yet she had died and despite his lack of presence in Castiel's life he had loved his father and had been determined to find him. Yes he had found his father but he was also gone just like Castiel's mother. The only people Castiel ever let get close to him had been Anna and, to some extent, Gabriel and yet now he had opened his life up to Dean and he had to admit that the thought of that terrified him.

Castiel was reaching for a mug to fill with coffee when there was a slight knock at the door.

"Hello Dean." Castiel said showing Dean into the apartment.

"Hey." Dean said giving Castiel a quick smile before he held up the iPod Castiel had forgotten he'd left in Dean's car. "Missing this?" Dean asked with a grin.

"Yes…thank you." Castiel said taking the iPod off Dean and throwing it onto the nearest countertop. "So…um…how are you?" Castiel said before Dean chuckled.

"Cas you saw me naked last night, please don't be awkward." Dean said.

"Sorry…sorry I've just been thinking through some things." Castiel said shrugging.

"Well that sounds…positive." Dean said with a derisive snort.

"Sorry, it was positive…kind of" Castiel said hating how awkward he sounded because he normally never sounded awkward. Sarcastic yes, awkward no.

"Cas I came over here because I needed to talk to you about some stuff but now I'm slightly freaked because you're acting strange and you never act strange. You're highly sardonic and a smartass but you're not that strange so what's up? Talk to me here Cas." Dean said.

"Ok." Castiel said shrugging.

"Ok?"

"Yes ok." Castiel said sighing slightly before he began to speak again. "So...so I think I'm in love with you but you're Dean Winchester-"

"Cas…" Dean started to say but Castiel held up his hand to stop him.

"No, please let me finish. You said you wanted me to talk so now I'm talking and if I don't get this out now then I probably never will and I'll be really pissed off with myself for not getting it out. I think I'm in love with you but you're Dean Winchester and that means that the entire of America, heck most of the world, knows who you are. You live in New York which is a twelve hour drive away because you're afraid of flying but most importantly you're an actor which means you're on set all the time, you travel a lot and that means that even though I think I'm in love with you I could go months at a time without seeing you. You'll be leaving here soon and I understand that though I probably should have said something before because now I'm going to have to sit here like a love scorned teenager…God maybe I should have something before now that I'm really thinking about it. I mean I'm a logical person. I am a smart and logical person who thinks over something at least ten times before I do it but I have yet to really think about anything to do with you since New York because I don't want to because when I think too much I end up running things for myself. I am a logical person, a logical person who is now slightly in love with an actor…an actor who has been in some terrible films and has won countless MTV awards, I mean _MTV_, the home of terrible, _terrible_ reality shows that both of my siblings love for reasons beyond me." Castiel said and as he carried on talking he began to feel lighter because he was fed up of bottling up all of his emotions. It was time to tell Dean everything. He had told Dean a lot the night before but now it was time to tell Dean everything. "I don't want to lose you ok? You may be some actor who was once in a cheesy cereal commercial but I still don't want to lose you."

"Cas-"

"Don't worry I'm done with the long speech now." Castiel said raising his hands up and Dean chuckled slightly.

"Look Cas…my…my life has been about nothing but acting and my career since I left school, my life has been a hectic mess since I was seventeen and I've gone from person to person, needless relationship to needless relationship for nearly ten years because I never felt truly there, I never felt like I had found someone who actually meant something to me apart from Sam, Jo and the other people who are my family. Now, partly thanks to my agent/publicist trying to hide part of my life, I met you. I've found you and I don't want to let you go either, ok Cas? I don't want to lose you either." Dean said watching as Castiel continued to look sorrowful. "I'm not going to lie to you ok because that would be cruel…if we're together it might not be easy. I'll be away for months at a time working on films that you will no doubt hate more than any other films." Castiel continued to stare at Dean with those damn huge blue eyes and it was really wasn't helping because Dean was trying to give a speech here god-dammit. "Look…I'm shit at relationships ok? I never know what to say and I never know what to do but, at the risk of sounding like a woman, I want to be with you because…well despite the fact that you're highly sarcastic, smarter than me and despise my films, oh and that I'm pretty sure that if I left you by yourself for more than a few days you would eat nothing but noodles and drink your weight in coffee. Despite all that I really do care about you…and…and I'm glad that you chose to care about me. I'm glad that you chose to love me"

"I think that's the longest time I've heard you speak for." Castiel said after a moment.

"You like giving long speeches, I like giving speeches ok and you're actually really lucky because that was a 'Dean Winchester' original and not from Braveheart." Dean said.

"You're a nerd." Castiel said shaking his head as he moved closer to Dean. He watched as Dean smirked slightly which sent a jolt of longing down into Castiel's stomach.

"So are you." Dean shot back as he moved even closer and pressed a light kiss against Castiel's lips. "Look…Cas I want to be with you and it's probably going to be difficult because I'll be away filming and my agent/publicist is an angry but possibly psychic deity who pretty much controls my entire life. I mean I can't even sneeze sometimes without Pamela being in control of it but I want this work out because I think that if I fuck this up then Jo might actually kill me." Dean then added.

"Then I have a suggestion for you" Castiel said.

"Oh really?"

"Yes, don't fuck this up." Castiel said before he pulled Dean back into the kiss that Dean started. The kiss started out light until it deepened and Castiel felt Dean's tongue against Castiel's lip. Castiel opened his mouth to let Dean's tongue in and even though he was still worried about what might happen Castiel wasn't going to let it get in the way of the fact that Dean was kissing him and Dean was a very good kisser.

* * *

The buzzing of Dean's phone interrupted their kissing and when Dean looked down to the screen he groaned slightly. Castiel looked at him questioningly and Dean gave him a frustrated sigh.

"It's my psychic angry agent/publicist/deity. I really need to take this." Dean said.

"Yeah sure, go ahead." Castiel said. "You can go in my room if you want some privacy." He added nodding towards his bedroom. Dean gave him a thankful smile before walking into Castiel's room and answering the phone.

"Yes Pamela?" Dean said as soon as he picked up the phone.

"Oh don't sound so scared I'm not ringing to yell at you because as far as I can tell you haven't done anything to piss me off yet. This call is actually about the independent film you've just been cast in. You know the one I told you about this morning?" Pamela said.

"Oh, ok" Dean said feeling relieved but at least Pamela wasn't yelling at him and she thought that he hadn't done anything to piss her off yet.

"It turns out that the filming is going to be taking place Chicago. The book the film is based on is set there and they want to keep the fans of the book happy by filming it in the place the book is set. The production company said something about twenty-something year old hipsters wanting their blood if they screw up the film so it's going to be filmed in Chicago. Filming starts in a few weeks and if there aren't any reshoots then it should be over in about three months. This means you'll have to rent a place to live if you don't want to stay in a hotel for three months. Does that sound ok?"

"Chicago? For three months…yeah…yeah that sounds ok to me." Dean said trying to fight the smile creeping across his face. Being in Chicago for three months meant that he didn't have to lose Castiel at all, he didn't have to go back to New York and try to make a long distance relationship work. He could stay in Chicago for at least three months.

"Wait is that Dean Winchester sounding not only happy but happy at something I said? I think I'm going to go into shock here." Pamela said chuckling slightly.

"Thanks Pamela…" Dean said smiling broadly.

"You're welcome Dean; I need to get going because I've got things to do but congratulations on the role. I'm really proud of you Dean."

"You're proud of me?" Dean asked.

"Yes but don't let that get to your head Dean." Pamela said chuckling before she said her goodbyes and hung up. Dean placed his phone back into his pocket and smiled to himself. Three months in Chicago…things were actually starting to really look up.

* * *

"Who was that?" Castiel asked once Dean was off the phone and returned to the main area of the apartment. Part of Dean felt like just torturing Castiel for a moment but he couldn't stop the slow smile creeping across his face. "What is it?" Castiel then asked.

"Well I've been interested in starring in this independent movie recently, it's based on some book from the nineties, and the script is really good. Well Pamela got back to me and told me that I got the role and everything-"

"Wow, that's great." Castiel said smiling though Dean could see that there was something behind the smile. "So…so you'll be leaving soon then won't you?"

"Not exactly." Dean said smirking because it felt quite nice to have the upper hand against Castiel for once. "That's what Pamela just rang me about you see. The book is based in Chicago and the production company want to keep the film as close to the book as possible. That means they're basing the film in Chicago, production starts next month according to Pamela and they'll be filming here for three months."

"Wait so…" Castiel said as his brow furrowed. "That means that…"

"Yeah, I'll be for at least three months filming." Dean said. The look of surprise on Castiel's face was completely adorable.

"You'll be here? As in here in Chicago and not leaving to go off somewhere else?"

"Yeah, I'll be here in Chicago."

"So what's the book?" Castiel asked and when Dean told him the title Castiel actually shook his head and chuckled loudly. "Dean Winchester…if you screw up one of my favourite books I swear I might actually kill you." Castiel added before he pulled Dean into what Dean hoped would be just one of many deep kisses.

* * *

**Author's Note: I'm sorry for the delay in updating. As I said there was internet issues which basically meant that I had no internet for several days and I went ever so slightly insane but now I have the internet back and clearly I'm updating. **

**Ok I lied. There aren't going to be just thirteen chapters. I'm writing an epilogue as well…why do I do this to myself? **


	14. Epilogue

_Two Months Later_

"Ok that's a wrap everyone!" the director called out and with a slight yawn Dean pulled himself up out the chair he'd been sat in for the past half an hour watching the end of filming for the day. Yawning once again Dean thought longingly of the large coffee he could pick up on his way home. There was a great coffee near his rented apartment that both he and Castiel loved plus Dean had been in there enough times over the past two months for most of the baristas to not stare at him when he walked in which was nice.

"Hey Dean!" one of Dean's co-stars, a redhead who went by the name of Charlie Bradbury, called as she sauntered over to Dean. Of all the people he had met on this shoot Charlie was by far the nicest person. The film was her first big acting job and, just like Castiel, she was a big fan of the book so most of the time she looked ridiculously happy just to be on set let alone playing one of the main characters. "Looking forward to going home?" Charlie then asked she and Dean headed towards their trailers to get changed out of their costumes.

"Yeah, it's been a long day." Dean said. He'd been on set since the early hours of the morning which had also meant dragging himself from a very warm Castiel-occupied bed that morning.

"Tell me about it. I can't wait to get back home, see my girlfriend and just go over my lines for tomorrow." Charlie said. During one of their trips to a local bar in Chicago Charlie had told Dean that she'd grown up in Rockford and still lived there so she just commuted to set every day. "Got anything planned for tonight?" Charlie then asked casually.

"I'm thinking that it's going to be a night of sitting on my couch with Castiel and maybe watch a film" Dean sad. Charlie was the only one on set who knew that Castiel was Dean's boyfriend because apparently she wasn't blind and she had seen 'the buckets of adorable' between dean and Castiel when he'd come onto set for a visit (in which Dean had witnessed Castiel nerd out over the set). Dean had made Charlie swear she wouldn't tell anyone but it was actually nice having someone to talk to about Castiel that wasn't Jo or Sam.

"That sounds nice." Charlie said as she reached her trailer. "Say 'Hi' to Castiel to me." Charlie added before she opened her trailer door.

"I will. See you tomorrow Charlie." Dean called.

* * *

Because of filming Dean had been renting a small apartment in Chicago for the past two months though he was getting frequent updates from Jo on the state of his apartment back in New York. Though these updates mainly including Jo complaining that there was nothing good to watch on HBO, that Dean's doorman was a lecherous asshat or that the Norwegian couple in the apartment opposite Dean's never shut their damn blinds and liked to walk around their apartment nude. These were hardly vital updates but at least Jo hadn't burnt the entire building down…yet. Dean's current rented apartment in Chicago wasn't too bad, it was small but then again Dean had never really liked large places as they made him feel uneasy and far too out in the open plus a great thing about the apartment was that it was only a five minute walk away from Castiel and Anna's apartment.

Dean let himself into the apartment while he checked his phone for messages. There were a few from Ellen and Bobby back home in Kansas just checking up on him, one from Jo telling him that she had burnt his largest frying pan trying to cook, two from Sam with just general updates on his day of classes and one from Castiel that afternoon complaining that the moron sat behind him in his afternoon lecture was more annoying than Gabriel which, according to Castiel, said an awful lot. Dean replied to the messages from Ellen, Bobby and Sam. He swiftly reminded Jo that he was planning on returning to New York soon as would like his apartment in a semi-liveable condition. After replying to those messages he quickly dialled Castiel's number.

"Hey." Dean said when Castiel picked up after the third ring. "I've finished filming for the day and I've just got back to my apartment, what are you up to?" Dean asked.

"Hello Dean. I'm just leaving the library as I speak actually." Castiel said and Dean wasn't remotely surprised by this at all. After Castiel's apartment and Dean's own apartment, the library was Castiel's main hideout and if he had the option to live there, even if it was only for the few remaining months that Castiel was at college, he probably jump, if Castiel ever jumped, at the chance. "I am very much done with studying for the day and I'm actually happy to see the end of my notes from the past week." Castiel explained with a slight sigh.

"Good, I have some lasagne from last night leftover and I haven't seen you for a good fourteen hours so why don't you hurry on over?" Dean said laughing.

"That couldn't sound more perfect. Anna and Gabriel are planning to Skype each other while watching this week's brand new episode of _Cupcake Wars_ and I cannot think of anything I would want to see less." Castiel said. Dean couldn't help might smirk at the sound of desperation in Castiel's voice. He'd witnessed Anna and Gabriel's Skype conversations over _Cupcake Wars_ and it was just as terrifying as Castiel made it sound. Both of them got frighteningly enthusiastic when it came to cake frosting.

"Well at least I know that I'm ranked higher than _Cupcake Wars_." Dean said with a chuckle as he pulled the lasagne he had made last night out of the fridge. During the two months he and Castiel had been together Dean had discovered that the quickest way to Castiel's heart, after books and kisses on his neck, was through well-made Italian food. Dean was starting to discover that well-made food in general made Castiel happy and he had to admit that it was freaking cute as hell.

"Don't worry Dean; an awful lot of things are ranked higher than _Cupcake Wars_." Castiel said and Dean heard slight rummaging from Castiel's end of the line. No matter he was throwing all of his notes and books back into the battered messenger bag he always carried around with him.

"Hopefully I make the top five."

"Oh that's a given, true you're ranked behind Anna and Ernest Hemingway but you're ahead of Gabriel."

"I should hope so. Gabriel may be your brother but I have a damn good ass and I'm adorable."

"You keep believing that Hollywood Ken." Castiel said and even through the phone Dean knew he was smirking.

* * *

"Hello there Dean" Castiel said when Dean opened the front door. Like always Castiel looked rumpled with his hair as scruffy as ever and his ever faithful University of Chicago hoodie that Dean was convinced Castiel was permanently attached to. Castiel's messenger bag, that would be full of books, notepads and Castiel's laptop, was slung over his shoulder like always. The whole look made Dean smile but none of that compared to the smile Castiel gave him as he walked into the apartment and quickly kissed Dean on the lips. "How was filming? Don't give me any spoilers just give me the overview of what you were doing today." Castiel said placing his bag down onto the floor. This was nothing new, while Castiel wanted to know how filming had gone, he never wanted to know any specifics in case of 'spoilers'. Most of the time Dean just ended up telling him about the one extra who always seemed to fall over when they were filming larger scenes or the fact that Dean's main co-star found impossible to say the word 'moist' without shuddering.

"Cas you've read the book, twenty-seven times I might add, you _know_ what happens so there is no possible way of me giving you spoilers." Dean said rolling his eyes.

"Yes but I don't know what they're adding to the film or not." Castiel said like it was the most obvious thing in the world.

"You know you could just read the script, it's always lying around here." Dean said rolling his eyes slightly. "If you read the script then you won't have to worry about them not adding any of your favourite scenes." Dean added.

"And ruin the surprise?!" Castiel said sounding completely scandalised by the very thought. This wasn't the first time, and it certainly wouldn't be the last time, that Dean had to admit that he was in love with a complete nerd.

"So if I were to tell you that today we were filming the scene in which Oliver-"

"Don't you dare Dean Winchester, don't you dare!" Castiel said.

"God you are such a damn nerd." Dean said shaking his head with a smile as he pulled Castiel into a quick kiss then went back to the kitchen while Castiel pulled off his hooded jumper. "So…what are you doing next weekend?" Dean asked as he pulled the left over lasagne out of the oven.

"I'll be reading and spending time with you no doubt." Castiel said with a small smile as he watched Dean quickly plate up their food.

"Well…" Dean started to say as he placed a liberal amount of lasagne onto Castiel's plate. "What do you say to reading and hanging out with me in California instead of here in Chicago?" Dean asked smirking when he watched Castiel's face change from a look of happiness to that of confusion.

"California?" Castiel asked as his brow furrowed.

"Yeah well I'm not needed on set because they're just filming the scenes when Catherine-"

"Dean don't you dare tell me what happens in the film!"

"Ok, ok you little nerd. Look, Sammy has finally relented and he's letting me meet his girlfriend, the fabled Jessica Moore, so how about you come with me to California for a few days and see the sun for the first time in several months? You finish early on Friday don't you? We could hit the road as soon as you finish your last class of the day." Dean said trying to sound casual but he desperately wanted to know what Castiel was thinking in that moment. "You know Sammy likes you and I'd like to be able to introduce you as my boyfriend." Dean added

"You want to introduce me to Sam as your boyfriend?" Castiel asked smiling with awe and that damn smile was the best damn smile in the world.

"Yes because it would be very awkward introducing you as my friend when I've seen you naked." Dean couldn't help but say with a huge smirking grin. "Plus I've never met Sam's girlfriend because he's a paranoid baby but going from the past girls he's liked she'll be incredibly plain and a nerd. You on the other hand, while being a nerd, are incredibly hot." Dean added entwining his fingers through the belt loops of Castiel's jeans and pulling him closer to Dean's chest.

"Ah I see, so you want to take me all the way to California to gloat to your brother is that it?" Castiel asked shaking his head slightly with a small smile across his lips before Dean planted a quick kiss on Castiel lips. Dean's teeth gently nicked Castiel's lower lip

"Well that and it will make me laugh like hell watching you try to rollerblade." Dean

"I am not rollerblading, I mean it. Over my dead body will I be rollerblading."

"Oh I'll get you rollerblading for my own amusement because I have _very_ effective methods of persuasion." Dean said grinding his hips against Castiel's. Castiel rolled his eyes and let out a small chuckle.

"You are hopeless." He said shaking his head at Dean.

"Yeah but you love me anyway." Dean said cockily as he gave Castiel a quick kiss on the forehead. "So, you'll come with me to California to see Sam and meet Jess?"

"As long as I get to pick half of the music we listen to on the way there."

"You can pick one song." Dean said then Castiel pouted, he actually _pouted_. "Fine" Dean said sighing. He'd never seen Castiel pout before. Dean had seen Castiel smirk, sneer and roll his eyes countless times before but he'd never seen Castiel pout. It was adorable even if weirdly creepy. "You can play _one _mix of your weird road trip music, happy now?" He asked and Castiel nodded with a triumphant smirk. "Good now come on then Milton, we can't let the food go cold." Dean said nodding towards the kitchen table. Castiel gave Dean another smirking smile before he went over to the table and sat down.

"You know, if you carry on cooking like this then I'm going to demand to quit being an actor and just become my permanent chef." Castiel said before digging into his food. Dean always thought the faces that Castiel made when he was eating food was hilarious, he always looked so damn pleased by the food that Dean made him. Then again Castiel lived off take-out, noodles and cereals so it was no real surprise that he always looked happy when eating.

"Would I have to wear one of those cheesy chef's hat or would I be one of those naked chefs?"

"The hats are called toques and I've seen how enthusiastically you cook bacon so under no circumstance should you cook naked no matter how attractive that sight would be." Castiel said winking at Dean before he went back to eating his lasagne.

* * *

Castiel rested his head against Dean's warm and solid chest with a contented sleepy smile as they lay on the couch together. Castiel wasn't a people person at all and he knew that, everyone that knew Castiel knew that he preferred the company of fictional characters to that of real people but when he was around Dean he forgot all of that and he found that he actually sought out Dean's company. When he was with Dean he never felt awkward and it never felt as if Dean was just being polite when listening to Castiel talk about books for hours on end, Dean was actually interested in what Castiel had to say even if it was just about the plot, of lack of, in the latest book he had read. Being with Dean made Castiel genuinely happy, happier than he had felt in a very long time and maybe their relationship wasn't normal because Dean was a multimillionaire actor with a star on the Hollywood walk of fame and they couldn't tell anyone about their relationship apart from the few people that already knew (basically Jo, Anna, Gabriel (who had been sworn to secrecy under pain of death) Charlie and Castiel's Aunt Rachel who only knew because Gabriel had blurted out something about 'Castiel's new boyfriend' the month previously) but Castiel didn't care at all because he really was happy.

Castiel found himself loving the time he spent with Dean even if it was just sat on Dean's couch watching an old movie like they were doing that evening.

Within the first month of being with him Castiel had discovered that Dean loved old western films as he'd had a cowboy phase (apparently Sam called it an obsession but Dean disagreed) during his childhood that he never really grew out of. Tonight's film was one Castiel had seen before and he wasn't really concentrating on the film anyway, he was more interested in just listening to the slow but steady sound of Dean's breathing as he rested his head against Dean's chest. There was something so relaxing about listening to Dean's breathing, it made him calm an anchored because as long as he was there listening to Dean's breathing that meant that Dean was still there, he was still with Castiel in that moment.

"Cas..." Dean said after a while which was a slight surprise because Dean normally never spoke during a film unless it was to quote dialogue or to ask to have Gabriel removed from the room during that one time Anna and Gabriel had watched Star Wars: A New Hope with them and Gabriel had proclaimed that film made no sense and that Han Solo was a lame character. During that moment Castiel was convinced that Dean might have killed Gabriel if Anna hadn't made Gabriel leave the room because of 'Jelly Bean related business'. "Um...Cas...I've been thinking..." Dean now said coughing slightly. He looked nervous which instantly set Castiel on edge because he knew their relationship had been going too well. "Well filming finishes soon so that means I'll be heading back to New York and you'll be finished with college and you're probably be thinking about moving back to Lincoln...I don't know..." Dean mumbled slightly.

"Dean...where are you going with this?" Castiel asked warily. He hasn't really thought about what he was going to do after he graduated, true he wanted to get into writing or publishing but he wasn't sure what he else wanted to do that didn't involve sitting on a couch kissing Dean while occasionally watching a film, sleeping next to Dean or being in the shower with Dean which wasn't so much showering as having sex while very wet. Castiel briefly wondered how that had become his life but then he remembered that Dean was saying stuff about moving back to New York so Castiel sat up and turned to properly look at Dean.

"Look I know it's only been like two months and you will probably think that it is a terrible idea, which it could be because I've seen your attempts at cooking and my kitchen in New York is far too nice to have peanut butter of the ceiling-"

"Those pancakes really were a bad idea in hindsight." Castiel said shrugging slightly.

"Oh yeah they were. But I don't really want to talk about pancakes...shit this sounded so much better in my head..." Dean said groaning quietly for a moment before he coughed and started talking again. "Look, as I said it might be a terrible idea because you cannot cook at all and I don't think I even own a vacuum let alone know where one is in my apartment plus Jo is always there drinking my beer and filling up my TiVo box with every show HBO broadcasts but still..."

"You do realise that you haven't told me the idea you think may or may not be a bad idea right?" Castiel asked easing an eyebrow with a slight smirk because Dean rambling and getting flustered was always highly amusing to him even now.

"Yeah...right...I think that - no, I want you to come to New York with me." Dean said sighing slightly in relief as he said it.

"What?" Castiel asked in surprise. First California and now this. Castiel was vaguely curious what had gotten into Dean but he decided that he would roll with it.

"At the end of the summer, you should come to New York and...you know...live with me. You like New York, it has enough bookstores to keep you ecstatically happy and there are music gigs nearly every night so you could fill your iPod up with even more unheard of bands. You could write and do whatever you wanted to do but you know, you could do it in New York." Dean said looking both scared and relieved at the same time like he was glad that he had asked Castiel this but he was also terrified that Castiel would say no.

As if that was even an option.

Leaving Illinois was something Castiel had been contemplating as long as it was for somewhere that he knew he would never want to leave and New York could easily be in of those places. It had the bookstores, the museums, the galleries, the theatres and all the culture.

New York had Dean.

New York had the one person Castiel was slowly becoming to depend on after his sister.

"I really don't know how to cook. I like play music loudly when I'm alone and I get weirdly obsessive compulsive about lime scale in bathrooms." Castiel heard himself say. "I view coffee as a main food group, I'm anti-social towards nearly everyone but you, my sister and occasionally Alfie and I once spent two days sat on my couch watching the extended directors edition of Lord of the Rings plus all the special features and by once I mean that it's something I do at least once a month. I spend an unhealthy amount of time hunched over books and my laptop so I'm probably going to be crippled by the time I turn thirty and even with all the stuff you already know about my family you're still not remotely prepared to know about or ever meet my Uncle Lucifer or my cousins Balthazar and Naomi because it's easier not to describe any of them all for very different reasons." Castiel babbled, his words spilling out of him without him realising. "I watch foreign films that could put most people to sleep and I hate the film E.T with a passion because the creepy little alien used to scare the hell out of me when I was younger so I was glad that he left that mopey kid even though Anna says that's heartless and...and-"

"And despite you being a caffeine dependant, anti-social nerd who is afraid of something that looks like walking twig I still love you and I still want you to live with me in New York. Besides I can deal with Gabriel in small doses so how bad can your cousins be?"

"Uncle Lucifer shipped Balthazar off to a boarding school in England to 'correct him' and now he's at university in London raining havoc in his own way. Naomi on the other hand is just...well she's a stickler for the rules and it can get tedious very quickly. Thankfully she's on some 'Save the world' mission with the Peace Corps, well that was the last I heard anyway, so I suppose I don't have to worry about them too much." Castiel said. "But you really want me to live with you? Despite the fact that I can't cook?"

"Yes Cas, I want you to live with me in New York despite the fact that you can't cook and you're a duvet hog."

"I like to cocoon" Castiel said shrugging while Dean smirked for a moment before pulling Castiel into a firm kiss. Even after two months it still felt like a force of nature was swelling up inside of his chest every time Castiel kissed Dean. Part of him hoped that feeling would never go away because he loved how breathless he felt even after the smallest of kisses.

"Cas I love you and believe me, I need you." Dean said with so much conviction that Castiel knew he would never doubt those words.

"It will be harder to hide though...you know, once we're back in New York." Castiel said as the thought dawned upon him. The press no longer believed that Dean and Anna were a couple after Dean had said in an interview that he and Anna were just good friends but there was a big difference between the press thinking Dean was dating and he press discovering that Dean was actually dating Castiel.

"Cas...I really don't want to hide you anymore. Look if you don't care that your face might be splashed across several gossip websites then if you do come with me to New York then I want to tell Pamela and the press. I love you and I don't want to hide that." Dean said. "I want to go somewhere and not be afraid to say 'Hey you see that scruffy looking nerd with the insane sex hair and the ridiculously blue eyes? Yeah well he's my boyfriend' it'll be a nice change."

"I think you've been in one too many cheesy chick flicks because that sounded really corny." Castiel said.

"Oh you take that back." Dean said punching Castiel lightly on the arm. "Take it back or I'm telling you about every scene we filmed today, in depths with spoilers and all." Dean said with a smirk.

"You wouldn't dare." Castiel said. Dean just carried on smirking. "You're bluffing."

"Well today we filmed the scene in which the guy from the subway-" Dean started to say but Castiel swiftly shut up him up pulling him into a deep kiss. Dean's hand slowly crept underneath Castiel's shirt until he was running his hand over Castiel's stomach and slowly moved to his waist. It was the lightest of touches but it sent shivers up Castiel's spine. Castiel really wondered how this had become his life. How had he gone from being just another college student to the boyfriend of America's most popular actor? Clearly he'd done something right somewhere even though all he'd really done was be sarcastic, mocking and slightly drunk in New York at one point. "So…what do you say about New York? Will you come with me?" Dean asked as he rested his forehead against Castiel's.

"No you really think I would say no?" Castiel asked smirking as he pulled Dean's lips back towards his own.

"I'm taking that as a 'yes'" Dean said between deep kisses. "But if you get peanut butter on my kitchen ceiling then I'm making you sleep in the bathtub." Dean added.

* * *

**Author's Note: God I want to say a huge thank you to everyone who read and loved this fic. I swear when I started it I never thought anyone would even want to read it so once again here a huge thank you. This probably won't be the last I'll write when it comes to this verse but I'll be focussing on drafting then writing my entry for the DeancasBigBang 2013 as well. **


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